KR20230063316A - Polycyclic aromatic compound - Google Patents

Abstract

A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the following formula (1) is useful as a material for an organic device such as an organic electroluminescent element. According to a preferred embodiment of the present invention, by manufacturing an organic electroluminescent element using a novel polycyclic aromatic compound, for example, as a host material in the light-emitting layer, as a component of the host material, or as a component of a layer adjacent to the light-emitting layer, the organic electroluminescent element with excellent quantum efficiency and element lifespan is provided.

Description

Polycyclic aromatic compound {POLYCYCLIC AROMATIC COMPOUND}

The present invention relates to a polycyclic aromatic compound, an organic electroluminescent device using the same, a display device, and a lighting device.

Conventionally, display devices using electroluminescent light-emitting elements can be reduced in power and reduced in thickness, so various researches have been conducted, and organic electroluminescent elements made of organic materials have been actively studied because they are easy to reduce in weight and increase in size. In particular, for the development of organic materials having luminescent properties such as blue or green, which are one of the three primary colors of light, and the development of organic materials having charge transport capabilities (possibly becoming semiconductors or superconductors) such as holes and electrons, Both high-molecular compounds and low-molecular compounds have been actively studied.

An organic EL element has a structure composed of a pair of electrodes composed of an anode and a cathode, and one layer or a plurality of layers disposed between the pair of electrodes and containing an organic compound. Layers containing organic compounds include a light emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

As light-emitting materials for the light-emitting layer, three types of fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials are currently used. For example, materials improved from azaborine derivatives have been reported as fluorescent materials (Patent Document 1), noble metal complexes having multidentate ligands, etc. have been developed as phosphorescent materials (Patent Document 2), and thermally activated type A carbazonitrile compound or the like has been developed as a delayed fluorescence (TADF) material (Non-Patent Document 1).

In any device using either material, a material having a high lowest excitation singlet energy level or lowest triplet excitation energy level is used as a host or adjacent layer of the light emitting layer to prevent energy leakage from the light emitting layer or neighboring layers leading to a decrease in efficiency. do.

Patent Document 1: International Publication No. 2015/102118 Patent Document 2: Japanese Unexamined Patent Publication No. 2014-239225

Non-Patent Document 1: Nature Vol.49213 December 2012

As described above, various materials have been developed as materials used for organic EL devices, but in order to increase the options of materials for organic EL devices, development of materials composed of compounds different from conventional ones is expected. In addition, in Patent Document 1, a polycyclic aromatic compound containing boron and an organic EL device using the same are reported, but in order to further improve device characteristics, materials for light emitting layers and materials for peripheral layers capable of improving luminous efficiency and lifetime of devices is being requested.

As a result of intensive studies to solve the above problems, the inventors of the present invention have succeeded in producing a novel polycyclic aromatic compound, and furthermore, have found that this compound is effective as a material having a high lowest excitation singlet energy level or lowest excitation triplet energy level. Found it. Then, for example, an organic EL device is formed by disposing a light emitting layer using such a polycyclic aromatic compound as a host material or a material of a layer adjacent to the light emitting layer and using a compound having a smaller triplet energy as a dopant material between a pair of electrodes. By configuring, an excellent organic EL element was found to be obtained, and the present invention was completed. That is, the present invention provides a polycyclic aromatic compound as described below, a material for an organic device containing the polycyclic aromatic compound as described below, and the like.

<1> A polycyclic aromatic compound having a structure composed of one or two or more structural units represented by the following formula (1);

In formula (1),

A is a monovalent group obtained by elimination of one hydrogen in the compound represented by formula (A),

Z is each independently >N or >CR ^Z ;

R ^Z are each independently hydrogen or any one substituent selected from substituent group Z,

Two adjacent R ^Z are bonded to each other, together with the carbon to which they are bonded, an aryl ring which may be substituted with at least one substituent selected from substituent group Z, or an aryl ring which may be substituted with at least one substituent selected from substituent group Z. may form a heteroaryl ring that is

Z ^X is carbon bonded by the other Z ^X and X ² , or >N or >CR ^Z ;

X ¹ and X ² are each independently a single bond, >O, >NR ^N1 , >BR ^B1 , >C(-R ^C1 ) ₂ , >Si(-R ^S1 ) ₂ , >S, >Se, -CR ^E1 =CR ^E1 -, or 1,2-phenylene, provided that when X ¹ is a single bond, X ² is not a single bond;

R ^N1 , R ^B1 and R ^E1 are each independently hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, Alkyl which may be substituted with at least one substituent selected from substituent group Z, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, R ^C1 and R ^S1 are each independently hydrogen, substituent group Aryl which may be substituted with at least one substituent selected from Z, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, or bonded to another R ^C1 or R ^S1 bonded to the same element to form a ring;

W is C, Si, or Ge;

Ring B is an aryl ring which may be substituted with at least one substituent selected from substituent group Z, or a heteroaryl ring which may be substituted with at least one substituent selected from substituent group Z,

at least one Y is >N,

at least one Y is >C-G, G is a group represented by formula (G);

In formula (G),

Z ^Y is >N or >CR ^Z ,

X ⁶ is a single bond, >C(-R ^C6 ) ₂ , >S, >O, >NR ^N6 , >Si(-R ^S6 ) ₂ , >Se, >Ge(-R ^G6 ) ₂ , -CR ^E6 =CR ^E6 -, or 1,2-phenylene, * is a binding site,

R ^N6 is hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, and at least one selected from substituent group Z Alkyl which may be substituted with a substituent, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, R ^C6 , R ^S6 , and R ^G6 are each independently hydrogen, at least one selected from substituent group Z Aryl which may be substituted with one substituent, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or substituent group Z Cycloalkyl which may be substituted with at least one selected substituent, or is bonded to another R ^C6 , R ^S6 , or R ^G6 bonded to the same element to form a ring, and R ^E6 is hydrogen, in substituent group Z aryl which may be substituted with at least one substituent selected from, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or substituent A cycloalkyl which may be substituted with at least one substituent selected from group Z,

the other Y's are each independently >CR ^Y ,

R ^Y is each independently hydrogen or a substituent selected from substituent group Z, R ^Y is a group other than the group represented by formula (G),

L is a single bond, arylene, heteroarylene, >O, >NR ^NL , >BR ^BL , >C(-R ^CL ) ₂ , >Si(-R ^SL ) ₂ , >S, or >Se;

R ^NL and R ^BL are hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, and at least one selected from substituent group Z Alkyl which may be substituted with one substituent, cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, R ^CL and R ^SL are each independently hydrogen, at least one substituent selected from substituent group Z aryl which may be substituted with, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or at least one selected from substituent group Z Cycloalkyl which may be substituted with one substituent, or bonded to another R ^CL or R ^SL bonded to the same element to form a ring;

At least one hydrogen in the above structure may be substituted with cyano, halogen, or deuterium,

Substituent group Z is,

aryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;

heteroaryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;

diarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded to each other via a linking group);

diheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two heteroaryls may be bonded to each other via a linking group);

Arylheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (aryl and heteroaryl may be bonded to each other via a linking group);

diarylboryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded via a single bond or a linking group);

Alkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;

cycloalkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;

alkoxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;

aryloxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl, and

It consists of substituted silyl.

<2> The polycyclic aromatic compound according to <1>, wherein X ⁶ is a single bond.

<3> The polycyclic aromatic compound according to <1> or <2>, which has the following partial structures;

In the formula, R ^G is R ^Y or G, and is bonded to L at *.

<4> The polycyclic aromatic compound according to <3>, wherein R ^G is phenyl or a group represented by formula (G).

<5> The polycyclic aromatic compound according to <1>, represented by any one of the following formulas.

<6> A material for organic devices containing the polycyclic aromatic compound according to any one of <1> to <5>.

<7> An organic electric field comprising a pair of electrodes composed of an anode and a cathode, and an organic layer disposed between the pair of electrodes, wherein the organic layer contains the polycyclic aromatic compound according to any one of <1> to <5>. light emitting element.

<8> The organic electroluminescent element according to <7>, wherein the organic layer is a light emitting layer.

<9> The organic electroluminescent device according to <8>, wherein the light-emitting layer contains the polycyclic aromatic compound as a host material and further includes a dopant material.

<10> The organic electroluminescent device according to <7>, wherein the organic layer is an electron transport layer.

<11> A display device or lighting device provided with the organic electroluminescent element according to any one of <7> to <10>.

According to a preferred embodiment of the present invention, by producing an organic EL device using a novel polycyclic aromatic compound as, for example, a host material in a light emitting layer, one component of the host material, or a component of a layer adjacent to the light emitting layer, quantum efficiency and device An organic EL element with excellent lifetime can be provided.

1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.
2 is an energy level diagram showing energy relationships among a host, an assisting dopant, and an emitting dopant of a TAF device using a typical fluorescent dopant.
3 is an energy level diagram showing an example of an energy relationship among a host, an assisting dopant, and an emitting dopant in an organic electroluminescent device according to one embodiment of the present invention.

In the following, the present invention will be described in detail. The description of the constitutional requirements described below may be made based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. In addition, in this specification, the numerical range expressed using "-" means the range which includes the numerical value described before and after "-" as a lower limit and an upper limit. In addition, in this specification, "hydrogen" in description of structural formula means "hydrogen atom (H)." Similarly, "carbon atom (C)" may be referred to as "carbon".

In this specification, "adjacent groups" means two groups respectively bonded to two adjacent atoms (two atoms directly bonded by covalent bonds) in the structural formula.

In the present specification, "Me" is methyl, "Et" is ethyl, "nBu" is n-butyl (normal butyl), "tBu" is t-butyl (tertiary butyl), "iBu" is isobutyl, "secBu" ” is secondary butyl, “nPr” is n-propyl (normal propyl), “iPr” is isopropyl, “tAm” is t-amyl, “2EH” is 2-ethylhexyl, “tOct” is t-octyl, “ Ad" is 1-adamantyl, "Ph" is phenyl, "Mes" is mesityl (2,4,6-trimethylphenyl), "Tf" is trifluoromethanesulfonyl, "TMS" is trimethylsilyl, "D" represents deuterium.

In this specification, an organic electroluminescent element is sometimes referred to as an organic EL element.

In the present specification, chemical structures and substituents are sometimes expressed as carbon atoms, but the number of carbon atoms in the case where a substituent is substituted in a chemical structure or a substituent is further substituted in a substituent means the number of carbon atoms in each chemical structure or substituent, , It does not mean the total number of carbon atoms of the chemical structure and substituents, or the total number of carbon atoms of substituents and substituents. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent A of carbon number X" is substituted for "substituent B of carbon number Y", and carbon number Y is substituent A and substituent It is not the carbon number of the sum of B. Further, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent A (with no carbon number limitation)" is substituted for "substituent B of carbon number Y", and carbon number Y is substituent A and It is not the carbon number of the sum of the substituents B.

<Description of rings and substituents>

First, details of the rings and substituents used in the present specification are described below.

Examples of the "hydrocarbon ring" in the present specification include a cycloalkane ring and a cycloalkene ring in addition to the "aryl ring" described later. A cyclopentane ring and a cyclohexane ring are mentioned as a specific example of a cycloalkane ring. Specific examples of the cycloalkene ring include a cyclopentene ring, a cyclohexene ring, a 1,3-cyclohexadiene ring, and a 1,4-cyclohexadiene ring.

As the "heteroring" in the present specification, non-aromatic heterocycles are exemplified in addition to the "heteroaryl ring" described later. Examples of the non-aromatic heterocyclic ring include a piperidine ring, a piperazine ring, and a morpholine ring.

Examples of the "aryl ring" in the present specification include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and aryl rings having 6 to 12 carbon atoms. An aryl ring of to 10 is particularly preferred.

Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic biphenyl ring, a condensed bicyclic naphthalene ring, an indene ring, and a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl). ), a condensed tricyclic ring, acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, anthracene ring, a condensed tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a chrysene ring, a condensed five ring perylene ring, A pentacene ring etc. are mentioned. The fluorene ring, benzofluorene ring, and indene ring also include structures in which fluorene rings, benzofluorene rings, cyclopentane rings, and the like are spiro bonded, respectively. On the other hand, in the fluorene ring, benzofluorene ring and indene ring, two of the two hydrogens of methylene in the structure are substituted with an alkyl such as methyl as the first substituent described later, respectively, to obtain a dimethylfluorene ring, dimethylbenzofluorene Rings and dimethylindene rings are also included.

Examples of the "heteroaryl ring" in the present specification include a heteroaryl ring having 2 to 30 carbon atoms, a heteroaryl ring having 2 to 25 carbon atoms is preferable, and a heteroaryl ring having 2 to 20 carbon atoms is more preferable. A heteroaryl ring having 2 to 15 carbon atoms is more preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. Examples of the "heteroaryl ring" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazane ring), a thiadiazole ring, a triazole ring, and a tetracyclic ring. sol ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzooxazole ring, benzothiazole ring, 1H-benzo Triazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, Phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, thianthrene ring, indolocarbazole ring, benzoindolocarbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, di A benzodioxin ring etc. are mentioned. In addition, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, two of the two hydrogens of methylene in the structure are substituted with alkyl such as methyl as the first substituent described later, respectively, to obtain a dimethyldihydroacridine ring, a dimethylxanthene ring, It is also preferable to be a dimethylthioxanthene ring or the like. Examples of the "heteroaryl ring" include bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, which are bicyclic rings, and terpyridyl rings, bispyridylphenyl rings, and pyridylbiphenyl rings, which are tricyclic rings. In addition, a "heteroaryl ring" shall also include a pyran ring.

In this specification, a substituent may be substituted with another substituent. For example, a specific substituent may be described as "substituted or unsubstituted". This means that the specific substituent is substituted with at least one other substituent or is not substituted. In some cases, "may be substituted" with the same meaning. In this specification, the specific substituent at this time may be referred to as a "first substituent" and the other substituent described above as a "second substituent".

In the present specification, the substituent group Z is,

aryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;

heteroaryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;

diarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded to each other via a linking group);

diheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two heteroaryls may be bonded to each other via a linking group);

Arylheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (aryl and heteroaryl may be bonded to each other via a linking group);

diarylboryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded via a single bond or a linking group);

Alkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;

cycloalkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;

alkoxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;

aryloxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl, and

It consists of substituted silyl.

The aryl as the second substituent in each group of the substituent group Z may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and similarly, the heteroaryl as the second substituent is aryl, heteroaryl, alkyl, or cycloalkyl. It may be substituted by alkyl.

In the present specification, when referring to a "substituent", it may be any one group selected from the substituent group Z, unless otherwise specified. For example, when a group to be "substituted or unsubstituted" is substituted, the group should just be substituted with at least one group selected from the substituent group Z.

In the present specification, “aryl” refers to, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 20 carbon atoms, aryl having 6 to 16 carbon atoms, aryl having 6 to 12 carbon atoms, or aryl having 6 to 12 carbon atoms. aryl of 10, etc.

Specific "aryl" includes, for example, monocyclic phenyl, bicyclic biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), condensed bicyclic naphthyl (1- naphthyl or 2-naphthyl), tricyclic terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl -3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4 -yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p -terphenyl-4-yl), condensed tricyclic, acenaphthylene-(1-, 3-, 4-, or 5-)yl, fluorene-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, Or 9-) day, tetracyclic quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl -4-yl, or m-quaterphenyl), condensed tetracyclic, triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-( 1-, 2-, or 5-)yl, or perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-) days, etc. In addition, the monovalent group of spirofluorene, etc. are mentioned.

In the aryl as the second substituent, the aryl is aryl such as phenyl (specific examples are groups described above), alkyls such as methyl (specific examples are groups described later), and cycloalkyls such as cyclohexyl or adamantyl. (Specific examples are groups described later) and structures substituted with at least one group selected from the group consisting of are also included.

One example thereof is a group in which the ninth position of fluorenyl as the second substituent is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl.

"Arylene" is, for example, arylene having 6 to 30 carbon atoms, and preferably includes arylene having 6 to 20 carbon atoms, arylene having 6 to 16 carbon atoms, arylene having 6 to 12 carbon atoms, or arylene having 6 to 12 carbon atoms. Arylene of 10, etc.

A specific "arylene" includes, for example, a divalent group obtained by removing one hydrogen from the aforementioned "aryl" (monovalent group).

"Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms. heteroaryl of 10; and the like. "Heteroaryl" contains one or more, preferably 1 to 5, heteroatoms selected from oxygen, sulfur, nitrogen, etc. in addition to carbon as ring-constituting atoms.

Specific examples of "heteroaryl" include pyrroleyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyr Dill, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindoleyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl , isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinil, phenothiazinil, phenazinyl, phenazacillinyl, indolizinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thienyl, benzothienyl, Isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl , indolocarbazolyl, benzoindolocarbazolyl, dibenzoindolocarbazolyl, imidazolinyl, or oxazolinyl, and the like. In addition, a monovalent group of spiro[fluorene-9,9'-xanthene], a monovalent group of spirobi[silafluorene], and a monovalent group of benzoselenophene are exemplified.

In the heteroaryl as the second substituent, the heteroaryl is aryl such as phenyl (specific examples are groups described above), alkyls such as methyl (specific examples are groups described later), and cyclohexyl or adamantyl such as cyclohexyl. Structures substituted with at least one group selected from the group consisting of alkyl (specific examples of which will be described later) are also included.

One example thereof is a group in which the ninth position of carbazolyl as the second substituent is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. In addition, groups in which nitrogen-containing heteroaryl such as pyridyl, pyrimidinyl, triazinyl, and carbazolyl is further substituted with phenyl or biphenylyl are also included in heteroaryl as the second substituent.

"Heteroarylene" is, for example, heteroarylene having 2 to 30 carbon atoms, preferably heteroarylene having 2 to 25 carbon atoms, heteroarylene having 2 to 20 carbon atoms, and heteroarylene having 2 to 15 carbon atoms. , or heteroarylene having 2 to 10 carbon atoms. In addition, "heteroarylene" is a divalent group such as a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of the "heteroarylene" include a divalent group obtained by removing one hydrogen from the aforementioned "heteroaryl" (monovalent group).

"Diarylamino" is amino in which two aryls are substituted, and the description of "aryl" described above can be cited for details of this aryl.

"Diheteroarylamino" is an amino group in which two heteroaryls are substituted, and the description of "heteroaryl" described above can be cited for details of this heteroaryl.

"Arylheteroarylamino" is an amino group in which aryl and heteroaryl are substituted, and the description of "aryl" and "heteroaryl" described above can be cited for details of the aryl and heteroaryl.

The two aryls in diarylamino as the first substituent may be bonded to each other via a linking group, and the two heteroaryls in diheteroarylamino as the first substituent may be bonded to each other via a linking group. The aryl and heteroaryl of arylheteroarylamino as a substituent may be bonded to each other through a linking group. Here, the description of "bonding via a linking group" indicates that, for example, two phenyls of diphenylamino form a bond with a linking group, as shown below. This statement also applies to diheteroarylamino and arylheteroarylamino, formed from aryls or heteroaryls.

Specifically as the linking group, >O, >NR ^X , >C(-R ^X ) ₂ , >Si(-R ^X ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se can be heard R ^X is each independently an alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. In addition, R ^X in >C(-R ^X ) ₂ and >Si(-R ^X ) ₂ may be bonded to each other through a single bond or a linking group ^XY to form a ring. Examples of X ^Y include >O, >NR ^Y , >C(-R ^Y ) ₂ , >Si(-R ^Y ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se. and R ^Y are each independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. However, when ^XY is >C(-R ^Y ) ₂ and >Si(-R ^Y ) ₂ , two R ^Y are bonded together to form no further ring. Furthermore, alkenylene is also mentioned as a linking group. Any hydrogen of the alkenylene may be each independently substituted with R ^X , and each R ^X is independently an alkyl, cycloalkyl, substituted silyl, aryl, and heteroaryl, which are alkyl, cycloalkyl, substituted silyl, or aryl. may be substituted.

In addition, in the present specification, when simply described as “diarylamino,” “diheteroarylamino,” or “arylheteroarylamino,” unless otherwise specified, each “two aryls of diarylamino are a linking group may be bonded through", "the two heteroaryls of the diheteroarylamino may be bonded to each other through a linking group", and "the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other through a linking group" It is assumed that an explanation such as "is added.

"Diarylboryl" is a boryl in which two aryls are substituted, and the description of "aryl" described above can be cited for details of this aryl. In addition, these two aryls are single bonds or linking groups (for example, -CH=CH-, -CR=CR-, -C≡C-, >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se). Here, the R of -CR=CR-, R of >NR, R of >C(-R) ₂ , and R of >Si(-R) are aryl, heteroaryl, diarylamino, alkyl, alkenyl , alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in R may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Moreover, two adjacent Rs may form a ring, and may form cycloalkylene, arylene, and heteroarylene. For the details of the substituents listed here, the description of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" described above, and "alkyl" and "alkyl" described later Descriptions of "kenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" can be cited. In addition, when it is simply described as "diaryl boryl" in this specification, unless otherwise limited, "two aryls of diaryl boryl may be bonded to each other through a single bond or a linking group". do as there is

"Alkyl" may be either straight chain or branched chain, and is, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, preferably, alkyl having 1 to 18 carbon atoms (C 3 to 24 carbon atoms). branched chain alkyl of 18), alkyl of 1 to 12 carbon atoms (branched chain alkyl of 3 to 12 carbon atoms), alkyl of 1 to 6 carbon atoms (branched chain alkyl of 3 to 6 carbon atoms), alkyl of 1 to 5 carbon atoms (3 carbon atoms) to 5 branched chain alkyl), C1-4 alkyl (C3-4 branched chain alkyl), and the like.

Specific "alkyl" includes, for example, methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1 ,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3 ,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethyl Butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl -1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1 -Methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl , n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl.

"Alkylene" is a divalent group obtained by removing any hydrogen from "alkyl", and is, for example, methylene, ethylene, or propylene.

Regarding "alkenyl", the description of "alkyl" described above can be referred to, and it is a group in which the C-C single bond in the structure of "alkyl" is substituted with a C=C double bond, and not only one but two or more groups Also includes groups in which a bond is substituted with a double bond (also called alkadien-yl or alkathien-yl).

"Alkenylene" is a divalent group obtained by removing any one hydrogen of "alkenyl", and examples thereof include vinylene.

Regarding "alkynyl", the description of "alkyl" described above can be referred to, and it is a group in which the C-C single bond in the structure of "alkyl" is substituted with a C≡C triple bond, and not only one but two or more groups Also includes groups in which a bond is substituted with a triple bond (also called alkadiyn-yl or alkathrin-yl).

"Cycloalkyl" is, for example, a cycloalkyl of 3 to 24 carbon atoms, preferably a cycloalkyl of 3 to 20 carbon atoms, a cycloalkyl of 3 to 16 carbon atoms, a cycloalkyl of 3 to 14 carbon atoms, or a cycloalkyl of 3 to 12 carbon atoms. cycloalkyl, cycloalkyl of 5 to 10 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, or cycloalkyl of 5 carbon atoms.

Specific "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyls having 1 to 5 carbon atoms or 1 to 4 carbon atoms (especially methyl) substituent, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1 ]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, or decahydroazulenyl, and the like.

"Cycloalkylene" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, or a cycloalkylene having 3 to 14 carbon atoms. , C3-C12 cycloalkylene, C5-C10 cycloalkylene, C5-C8 cycloalkylene, C5-C6 cycloalkylene, or C5 cycloalkylene.

Specific examples of "cycloalkylene" include a structure made into a divalent group by removing one hydrogen from the aforementioned "cycloalkyl" (monovalent group).

"Cycloalkenyl" is a group having a structure in which at least one set of single bonds between two carbon atoms in the above-mentioned "cycloalkyl" is a double bond (for example, -CH ₂ -CH ₂ - is - a group substituted with CH=CH-), and groups not corresponding to aryl are exemplified. Specifically, 1-cyclohexenyl, 1-cyclopentenyl, etc. are mentioned.

"Alkoxy" is a group represented by "Alk-O- (Alk is alkyl)", and the description of "alkyl" described above can be cited for details of this alkyl.

"Aryloxy" is a group represented by "Ar-O- (Ar is aryl)", and the description of "aryl" described above can be cited for details of this aryl.

"Substituted silyl" is, for example, silyl substituted with at least one of aryl, alkyl, and cycloalkyl, preferably triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyl dicycloalkylsilyl.

"Triarylsilyl" is a silyl group substituted with three aryls, and the description of "aryl" described above can be cited for details of this aryl.

Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

"Trialkylsilyl" is a silyl group substituted with three alkyls, and the description of "alkyl" described above can be cited for details of this alkyl.

Specific "trialkylsilyl" includes, for example, trimethylsilyl, triethylsilyl, trin-propylsilyl, triisopropylsilyl, trin-butylsilyl, triisobutylsilyl, tris-butylsilyl, trit- Butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldi Ethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldin- propylsilyl, s-butyldin-propylsilyl, t-butyldin-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, or t-butyldiisopropylsilyl and the like.

"Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyls, and the description of "cycloalkyl" described above can be cited for details of this cycloalkyl.

Specific "tricycloalkylsilyl" is, for example, tricyclopentylsilyl or tricyclohexylsilyl.

"Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and the descriptions of "alkyl" and "cycloalkyl" described above can be cited for details of these alkyls and cycloalkyls. .

"Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyls, and for details of these alkyls and cycloalkyls, the descriptions of "alkyl" and "cycloalkyl" described above can be cited. .

<When two groups bonded to the same atom bond to each other>

In the present specification, when it is said that two groups bonded to the same atom may be bonded to each other to form a ring, they may be bonded by a single bond or a linking group (these are collectively referred to as a linking group), and the linking group is -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, examples thereof include the following structures. Meanwhile, the R of -CHR-CHR-, the R of -CR ₂ -CR ₂ -, the R of -CR=CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and R in -Si(-R) ₂ - are each independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl which may be substituted with cycloalkyl , alkenyl which may be substituted with alkyl or cycloalkyl, alkynyl which may be substituted with alkyl or cycloalkyl, or cycloalkyl which may be substituted with alkyl or cycloalkyl. Moreover, two adjacent Rs may form a ring, and may form cycloalkylene, arylene, and heteroarylene.

As a bonding group, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a single bond or a linking group. Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond or linking group are more preferable, and a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are more preferred, and a single bond is most preferred.

The position at which two R are bonded by a bonding group is not particularly limited as long as it can be bonded, but it is preferable to bond at the most adjacent position, for example, when the two groups are phenyl, "C" in phenyl or It is preferable to bond to each other at ortho (second position) positions based on the bonding position (first position) of "Si" (see the above structural formula).

1. Bonn inventive dahwan aromatic compounds

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (1).

In formula (1), A is a monovalent group obtained by elimination of one hydrogen in the compound represented by formula (A), and at least one Y is nitrogen (>N).

The present inventors have found that the polycyclic aromatic compound of the present invention in which a nitrogen-containing aromatic ring having a specific substituent such as triazine and a bulky polycyclic structure (a polycyclic structure including a spiro bond or a spiro-approximate structure) is linked has a high minimum triplet excitation energy. It has been found that high efficiency and long lifetime are imparted when used as a host compound or electron transport layer material of a phosphorescent organic EL device or an organic EL device using thermally activated delayed fluorescence.

The compound represented by formula (1) is a 6-membered group containing a monovalent group obtained by elimination of one hydrogen in the compound represented by formula (A) by a linking group represented by L and at least one nitrogen as a ring atom. It has a structure in which ventilation is combined. Each part is described below.

<Six-membered ring containing nitrogen as a ring-constituting atom>

The compound represented by formula (1) contains a 6-membered ring group represented by the following formula (1-AL). The group represented by formula (1-AL) bonds with L in *.

In formula (1-AL), at least one Y is >N. It is preferable that 2 or 3 Y's are >N, more preferably, 3 Y's are >N, and it is even more preferable that 3 Y's are >N and form a triazine ring.

In formula (1-AL), at least one Y is >C-G, and G is a group represented by formula (G).

In formula (G),

Z ^Y are each independently >N or >CR ^Z. R ^Z has the same meaning as R ^Z in Z described later. It is preferable that any one or two of Z ^Y is >N, and the others are >CR ^Z , or all are >CR ^Z , and it is more preferable that all are >CR ^Z. It is preferable that all of R ^Z are hydrogen.

X ⁶ is a single bond, >C(-R ^C6 ) ₂ , >S, >O, >NR ^N6 , >Si(-R ^S6 ) ₂ , >Se, >Ge(-R ^G6 ) ₂ , -CR ^E6 =CR ^E6 -, or 1,2-phenylene, Z ^Y is >N or >CR ^Z , and * is a binding position.

R ^N6 is hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, and at least one selected from substituent group Z Alkyl which may be substituted with a substituent, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, preferably aryl which may be substituted with aryl or heteroaryl, substituted with aryl or heteroaryl It is preferably an optional phenyl, and more preferably an unsubstituted phenyl. R ^C6 , R ^S6 , and R ^G6 are each independently hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, Alkyl which may be substituted with at least one substituent selected from substituent group Z, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, aryl which may be substituted with aryl or heteroaryl, aryl or It is preferable that it is heteroaryl which may be substituted by heteroaryl, or unsubstituted alkyl. It is preferred that both R ^C6 's are methyl. It is preferable that all of R ^S6 are methyl. In addition, it is preferable that all of R ^G6 are methyl. Two R ^C6 's may be bonded to each other to form a ring, two R ^S6 's may be bonded to each other to form a ring, or two R ^G6 's may be bonded to each other to form a ring. R ^E6 is hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, and at least one substituent selected from substituent group Z Alkyl which may be substituted with or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, all of which are preferably hydrogen or methyl, more preferably all of which are hydrogen.

X ⁶ is preferably a single bond, >C(-R ^C6 ) ₂ , >S, >O, or >NR ^N6 , more preferably a single bond, >S, or >O, and a single bond. more preferable than

It is preferable that it is carbazolyl which may have a substituent, and, as for the group represented by Formula (G), it is more preferable that it is unsubstituted carbazolyl.

Y other than Y which is >N or >CG is each independently >CR ^Y , and R ^Y is each independently hydrogen or a substituent selected from substituent group Z. Although the substituent selected from substituent group Z may correspond to G, R ^Y is a group other than G (group represented by formula (G)). R ^Y is preferably hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, more preferably hydrogen or aryl which may be substituted with aryl or heteroaryl, and hydrogen or aryl or heteroaryl It is more preferable that it is phenyl which may be substituted, and it is especially preferable that it is hydrogen or unsubstituted phenyl.

The group represented by formula (1-AL) is preferably a group represented by the following formula.

In the formula, R ^G is R ^Y or G, and is bonded to L at *. In the formula, R ^G is preferably G, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl (other than G), more preferably G or aryl which may be substituted with aryl or heteroaryl. , G or phenyl which may be substituted with aryl or heteroaryl is more preferable, and it is particularly preferable that it is G or unsubstituted phenyl.

<L>

L is a single bond, arylene, heteroarylene, >O, >NR ^NL , >BR ^BL , >C(-R ^CL ) ₂ , >Si(-R ^SL ) ₂ , >S, or >Se. Although arylene and heteroarylene may have a substituent such as a substituent selected from substituent group Z, it is preferably unsubstituted.

R ^NL and R ^BL are hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, and at least one selected from substituent group Z Alkyl which may be substituted with one substituent, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, preferably aryl which may be substituted with aryl or heteroaryl, with aryl or heteroaryl It is preferable that it is phenyl which may be substituted, and it is more preferable that it is unsubstituted phenyl. R ^CL and R ^SL are each independently hydrogen, aryl which may be substituted with at least one substituent selected from substituent group Z, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, in substituent group Z Alkyl which may be substituted with at least one selected substituent, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, optionally substituted with aryl or heteroaryl, substituted with aryl, aryl or heteroaryl It is preferable that it is heteroaryl which may be, or unsubstituted alkyl. Two R ^{CL '} s may be bonded to each other to form a ring, and two R ^{SL '} s may be bonded to each other to form a ring.

L is preferably a single bond, arylene or heteroarylene, more preferably a single bond or heteroarylene. As the heteroarylene, a divalent group of dibenzofuran or dibenzothiophene is preferable. The binding position is preferably at positions 2 and 4, and positions 2 and 8.

<Formula (A)>

In formula (A), W is C, Si, or Ge. When two Z ^X are bonded, W becomes a spiro atom. It is preferable that W is C.

In Formula (A), Z is each independently >N or >CR ^Z , R ^Z is each independently hydrogen or any one substituent selected from substituent group Z, and two adjacent R ^Z are mutually Combined, together with the carbon to which they are bonded, an aryl ring which may be substituted with at least one substituent selected from substituent group Z or a heteroaryl ring which may be substituted with at least one substituent selected from substituent group Z is formed, may be

The substituent ^RZ (other than hydrogen) and the substituent of the ring formed as described above are preferably aryl which may be substituted with aryl or heteroaryl or heteroaryl which may be substituted with aryl or heteroaryl.

As for Z, it is preferable that one or two of them are >N, the others are >CR ^Z , or all are >CR ^Z , and it is more preferable that all of them are >CR ^Z. It is preferable that all of R ^Z are hydrogen.

Z ^X is a carbon bonded to the other Z ^X by X ² , or >N or >CR ^Z. That Z ^X is carbon bonded to the other Z ^X by X ² means that both Z ^X 's are carbon and are bonded to each other by X ² at the site indicated by the broken line in Formula (A). It is preferable that Z ^X is carbon bonded to the other Z ^X by X ² , or both are >CH.

X ¹ and X ² are each independently a single bond, >O, >NR ^N1 , >BR ^B1 , >C(-R ^C1 ) ₂ , >Si(-R ^S1 ) ₂ , >S, >Se, -CR ^E1 =CR ^E1 -, or 1,2-phenylene. However, when X ¹ is a single bond, X ² is not a single bond. R ^N1 , R ^B1 and R ^E1 are each independently hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, It is alkyl which may be substituted with at least 1 substituent selected from substituent group Z, or cycloalkyl which may be substituted with at least 1 substituent selected from substituent group Z. R ^N1 and R ^B1 are preferably aryl which may be substituted with aryl or heteroaryl, preferably substituted or unsubstituted phenyl, and still more preferably unsubstituted phenyl. It is preferable that all of R ^E1 are hydrogen or methyl, and it is more preferable that all of them are hydrogen. R ^C1 and R ^S1 are each independently hydrogen, aryl which may be substituted with at least one substituent selected from substituent group Z, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, and substituent group Z Alkyl which may be substituted with at least one selected substituent, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, optionally substituted with aryl or heteroaryl, substituted with aryl, aryl or heteroaryl It is preferable that it is heteroaryl which may be, or unsubstituted alkyl. Two R ^{C1 '} s may be bonded to each other to form a ring, and two R ^{S1 '} s may be bonded to each other to form a ring.

X ¹ is preferably >O, >NR ^N1 , or >S. X ² is preferably a single bond.

Ring B is an aryl ring which may be substituted with at least one substituent selected from substituent group Z, or a heteroaryl ring which may be substituted with at least one substituent selected from substituent group Z, and in formula (A), the ring It is a divalent group having bonds with each of the two adjacent ring constituent elements. When the above aryl ring and heteroaryl ring have a substituent, the substituent is preferably aryl which may be substituted with aryl or heteroaryl, heteroaryl which may be substituted with aryl or heteroaryl, or unsubstituted alkyl. Ring B is preferably an unsubstituted aryl ring or an unsubstituted heteroaryl ring. As the aryl ring, a benzene ring is preferable, and as the heteroaryl ring, a benzofuran ring, a dibenzofuran ring, a benzothiophene ring, or a dibenzothiophene ring is preferable.

<Monovalent group obtained by elimination of one hydrogen in the compound represented by formula (A)>

In Formula (A), one hydrogen to be desorbed may be at any position. The desorbed hydrogen is preferably a hydrogen at a position other than the B ring. Specifically, any one of Z, Z ^X , or R ^N1 , R ^B1 , R ^C1 , R ^S1 , R ^E1 in any one of X ¹ or X ² may be hydrogen in 1,2-phenylene. Preferable examples include hydrogen in Z where >CH, hydrogen in R ^N1 , and hydrogen in any of phenyl in R ^N1 which is phenyl.

<Combination of each substructure>

The combination of the 6-membered ring group represented by the above formula (1-AL), L, and the monovalent group obtained by elimination of one hydrogen in the compound represented by the formula (A) is not particularly limited.

<Specific example>

As a preferred specific example of the structural unit represented by the following formula (1), the formula (1) is formula (1-a) to formula (1-i), formula (2-a) to formula (2-i), formula (3-a) - the structural unit represented by any one of formula (3-i) is mentioned.

In the formula, at least one Y is >N, the others are >CR ^Y , and in Z, Z ^X , X ¹ , L, R ^Y , Z, Z ^X , X ¹ , L, R in formula (1) Each has the same meaning as in ^Y , the same preferred range, X ³ is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and >NR R of is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si(-R ) R of ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,

One of R ¹ and R ² is a group represented by formula (G) and the other is a group represented by formula (G), or a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl.

In each of formulas (1-a) to formulas (1-i), formulas (2-a) to formulas (2-i), and formulas (3-a) to formulas (3-i), Y is all > It is preferably N. X ³ is preferably >O or >S. Each of R ¹ and R ² is a group represented by formula (G), or preferably one of which is a group represented by formula (G) and the other is unsubstituted aryl, both of which are unsubstituted carbazolyl, or It is more preferable that one is unsubstituted carbazolyl and the other is unsubstituted phenyl.

<Structure consisting of one or more structural units>

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (1). The polycyclic aromatic compound having a structure composed of one structural unit is a polycyclic aromatic compound represented by the formula described above as a structural unit represented by formula (1). The polycyclic aromatic compound having a structure composed of two or more structural units represented by formula (1) is a compound corresponding to a multimer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1). . As for a multimer, a 2-hexamer is preferable, a 2-3mer is more preferable, and a dimer is especially preferable. The multimer may be in the form of having a plurality of the unit structures in one compound, or may be in the form in which an arbitrary ring contained in the structural unit is shared by a plurality of unit structures and bonded, and also any unit structure included in the unit structure What is necessary is just the form in which the rings of are bonded by condensation. Moreover, the form in which the said unit structure couple|bonded with multiple coupling groups, such as a single bond and C1-C3 alkylene, phenylene, and naphthylene, may be sufficient. Among these, a form in which rings are shared and bonded is preferable.

<Description of Substitution with Deuterium, Cyano or Halogen>

At least one hydrogen in the polycyclic aromatic compound of the present invention may be substituted with heavy hydrogen, cyano or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

<Stereoisomer>

The polycyclic aromatic compound of the present invention may have enantiomers or diastereomers. Regardless of the structural formula described, any stereoisomer in any one pure form, any mixture of stereoisomers, racemates, etc. , all of which are included in the scope of the present invention.

<Specific examples of polycyclic aromatic compounds of the present invention>

Specific examples of the polycyclic aromatic compound of the present invention include compounds represented by any one of the following structural formulas.

2. dahwan Method for producing aromatic compounds

The compound represented by formula (1) is a compound having a reactive group at a desired position of a nitrogen-containing 6-membered ring in formula (1) and a compound having a reactive group at a desired position of L or a compound represented by formula (A) as starting materials As such, it can be manufactured by applying Suzuki coupling, Negishi coupling, and other well-known coupling reactions. Examples of the reactive group of these reactive compounds include halogen and boronic acid.

3. organic device

The polycyclic aromatic compound according to the present invention can be used as a material for organic devices. As an organic device, an organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell etc. are mentioned, for example.

3-1. abandonment electric field light emitting element

Hereinafter, the organic EL element according to the present embodiment will be described in detail based on the drawings. 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.

<Structure of organic electroluminescent device>

The organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer ( 103), the hole transport layer 104 provided on the hole transport layer 104, the light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, and the electron injection provided on the electron transport layer 106 It has a layer (107) and a cathode (108) provided on the electron injection layer (107).

In addition, the organic EL element 100 is manufactured by reversing the manufacturing order, for example, the substrate 101, the cathode 108 provided on the substrate 101, and the electron injection layer provided on the cathode 108 ( 107), an electron transport layer 106 provided on the electron injection layer 107, a light emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light emitting layer 105, and a hole transport layer It is good also as a structure which has the hole injection layer 103 provided on 104, and the anode 102 provided on the hole injection layer 103.

It is not necessary to have all of the above layers, and the minimum structural unit is composed of an anode 102, a light emitting layer 105, and a cathode 108, and the hole injection layer 103, the hole transport layer 104, and the electron transport layer ( 106), the electron injection layer 107 is an arbitrarily provided layer. In addition, each said layer may consist of a single layer, respectively, and may consist of multiple layers.

As an aspect of the layer constituting the organic EL element, in addition to the constitutional aspect of the above-described "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/ Emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/emission layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/hole transport layer/emission layer/electron injection layer" / cathode", "substrate/anode/hole injection layer/hole transport layer/emission layer/electron transport layer/cathode", "substrate/anode/emission layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/emission layer" /electron injection layer/cathode", "substrate/anode/hole transport layer/light emitting layer/electron transport layer/cathode", "substrate/anode/hole injection layer/light emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer" /Light emitting layer/electron transport layer/cathode”, “substrate/anode/light emitting layer/electron transport layer/cathode”, or “substrate/anode/light emitting layer/electron injection layer/cathode” may be used.

The organic EL element may further have any one or both selected from an electron blocking layer (electron blocking layer) and a hole blocking layer (hole blocking layer). The electron blocking layer has a LUMO shallower than that of the light emitting layer and a HOMO close to that of the light emitting layer or the hole transport layer, and is disposed between the light emitting layer and the hole transport layer. Since electrons stay in the light emitting layer and do not leak into the hole transport layer, shortening of life due to deterioration of the hole transport layer and decrease in efficiency due to reduction in recombination efficiency can be prevented. The hole blocking layer has a HOMO deeper than that of the light emitting layer and a LUMO close to that of the light emitting layer or the hole transporting layer, and is disposed between the light emitting layer and the electron transporting layer. Since the holes stay in the light emitting layer and do not leak into the electron transport layer, shortening of life due to deterioration of the electron transport layer and decrease in efficiency due to reduction in recombination efficiency can be prevented. The hole injection/transport layer may also serve as an electron blocking layer. The electron injection/transport layer may also serve as a hole blocking layer.

The organic EL element may further have a high T1 layer. The high T1 layer has a T1 higher than that of the host compound, assisting dopant compound or emitting dopant compound used in the light emitting layer, and is disposed between the light emitting layer and the hole transport layer and/or between the light emitting layer and the electron blocking layer. The value of T1 energy varies depending on the light emission mechanism of the device, but has a higher T1 than the compound used for the host. By having a high T1 layer around the light emitting layer, the triplet energy is confined and the triplet energy, which is not normally converted to light emission in fluorescent molecules, is converted into singlet energy, so that high efficiency can be obtained. The hole injection/transport layer or the electron blocking layer may serve as the high T1 layer. The electron injection/transport layer or the hole blocking layer may serve as the high T1 layer.

The polycyclic aromatic compound of the present invention is preferably used as a material for an organic electroluminescent device. In general, a compound having a donor structure can be used for a hole transporting host material and a hole transporting layer in a light emitting layer, and a compound having an acceptor structure can be used for an electron transporting host material and an electron transporting layer, and a donor structure and an acceptor structure A compound having both can be used for any of the host and electron transport layer in a hole transport layer and a light emitting layer. For the donor structure and the acceptor structure, reference may be made to, for example, Advanced Functional Materials 2020, 2008332, and the like. More specifically, the donor structure includes a triarylamine structure and a carbazole structure, and the acceptor structure includes a triazine structure, a pyrimidine structure, and a pyridine structure. The polycyclic aromatic compound according to the present invention can be used as a host material, a hole transport layer material, an electron transport layer material, or the like in a light emitting layer.

<Substrate in organic electroluminescence device>

The substrate 101 is a support for the organic EL element 100, and usually quartz, glass, metal, plastic or the like is used. The substrate 101 is formed in the shape of a plate, film, or sheet depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Especially, a glass plate and a board made of transparent synthetic resins, such as polyester, polymethacrylate, polycarbonate, and polysulfone, are preferable. In the case of a glass substrate, soda-lime glass, non-alkali glass, etc. are used, and thickness should just have enough thickness to maintain mechanical strength. Further, a gas barrier film such as a dense silicon oxide film may be formed on at least one side of the substrate 101 to improve gas barrier properties, and in particular, a plate, film or sheet made of synthetic resin having low gas barrier properties is used as the substrate. When used as (101), it is preferable to form a gas barrier film.

<Anode in Organic Electroluminescence Device>

The anode 102 serves to inject holes into the light emitting layer 105 . Meanwhile, when at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through them. .

Materials forming the anode 102 include inorganic compounds and organic compounds. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO)) etc.), metal halides (such as copper iodide), copper sulfide, carbon black, ITO glass and Nessa glass. As an organic compound, conductive polymers, such as polythiophene, such as poly(3-methylthiophene), polypyrrole, and polyaniline, etc. are mentioned, for example. In addition, it can be used suitably selected from materials used as anodes of organic EL elements.

<Hole Injection Layer, Hole Transport Layer in Organic Electroluminescent Device>

The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light emitting layer 105 or into the hole transport layer 104 . The hole transport layer 104 serves to efficiently transport holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105 . The hole injection layer 103 and the hole transport layer 104 are formed by laminating or mixing one type or two or more types of hole injection/transport materials, respectively. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection/transport material.

As the hole injection/transport material, it is necessary to efficiently inject/transport holes from the positive electrode between electrodes to which an electric field is applied, and it is preferable to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable that the material has a small ionization potential, a high hole mobility, and excellent stability, and is difficult to generate trap impurities during production and use. As a material for the hole transport layer, it is also preferable to use the polycyclic aromatic compound of the present invention.

As the material forming the hole injection layer 103 and the hole transport layer 104, in the photoconductive material, a compound conventionally used as a hole charge transport material, a p-type semiconductor, a hole injection layer of an organic EL device, and a hole Any compound may be selected and used from known compounds used in the transport layer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine Derivatives (polymers having aromatic tertiary aminos in the main or side chains, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di (3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl -N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'- Diphenyl-1,1'-diamine, N ⁴ ,N ^{4 '} -diphenyl-N ⁴ ,N ^4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-bi phenyl] -4,4'-diamine, N ⁴ ,N ⁴ ,N ^{4 '} ,N ^4' -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]- Triphenylamine derivatives such as 4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (no metals, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone-based compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaaza triphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonates or styrene derivatives having the above monomers in their side chains , polyvinylcarbazole, polysilane, etc. are preferable, but it is not particularly limited as long as it is a compound capable of forming a thin film necessary for manufacturing a light emitting device, injecting holes from an anode, and transporting holes.

It is also known that the conductivity of an organic semiconductor is strongly influenced by its doping. Such an organic semiconductor matrix material is composed of a compound having good electron donating property or a compound having good electron accepting property. For doping of electron donor materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are used. known (see, for example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998) and J. Blochwitz , M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material varies considerably. As matrix materials having hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburstamine derivatives (TDATA, etc.), or specific metal phthalocyanines (particularly, zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Publication) Publication No. 2005-167175).

The material for the hole injection layer and the material for the hole transport layer described above are a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a main chain polymer and the reactive compound reacted A pendant-type polymer compound or a pendant-type polymer crosslinked product thereof can also be used for the hole layer material.

<Light-emitting layer in organic electroluminescent device>

The light-emitting layer 105 is a layer that emits light by recombination of holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light emitting layer 105 may be a compound (luminescent compound) that is excited by recombination of holes and electrons and emits light. It is preferable that it is a compound which shows. It is also preferable to use the polycyclic aromatic compound of the present invention as a material for a light emitting layer.

The light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting layer material (host material, dopant material). The host material and the dopant material may be of one type, a combination of a plurality of materials, or any of them. The dopant material may be included in the entire host material, or partially included, or any of them may be used. As the doping method, it can be formed by co-evaporation with the host material, but it may be deposited simultaneously after mixing with the host material in advance, or formed into a film by wet film forming after mixing with the host material in advance with an organic solvent.

The amount of host material used varies depending on the type of host material, and may be determined according to the characteristics of the host material. The standard for the amount of host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, still more preferably 90 to 99.9% by mass with respect to the total mass of the material for the light emitting layer.

The amount of dopant material used varies depending on the type of dopant material, and may be determined according to the characteristics of the dopant material. The reference amount of the dopant material used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, still more preferably 0.1 to 10% by mass with respect to the total mass of the material for the light emitting layer. The above range is preferable in that, for example, the concentration quenching phenomenon can be prevented. From the standpoint of durability, it is also preferable that part or all of the hydrogen in the dopant material is deuterated.

As the dopant material, you may use an emitting dopant and an assisting dopant material. As the assisting dopant material, it is preferable to use a thermally activated delayed fluorescent material. In an organic EL device using an assisting dopant material, it is preferable that the amount of the emitting dopant material used is low in concentration to prevent concentration quenching. A high concentration of the assisting dopant material is preferred from the viewpoint of the efficiency of the thermally activated delayed fluorescence device. In addition, in an organic electroluminescent device using a thermally activated delayed fluorescence assisting dopant material, in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant material, the amount of the assisting dopant material is compared to the amount of the assisting dopant material. It is preferable that the amount used is low concentration.

In the case where an assisting dopant material is used, the standards for the amounts of the host material, the assisting dopant material, and the emitting dopant material used are 40 to 99% by mass and 59 to 1% by mass, respectively, with respect to the total mass of the material for the light emitting layer. and 20 to 0.001% by mass, preferably 60 to 95% by mass, 39 to 5% by mass and 10 to 0.01% by mass, more preferably 70 to 90% by mass, 29 to 10% by mass and It is 5-0.05 mass %.

<Host Material>

As the host material, condensed ring derivatives such as anthracene and pyrene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, Benzofluorene derivatives, N-phenylcarbazole derivatives, carbazonitrile derivatives, etc. are mentioned.

The triplet energy of the host material is preferably higher than the triplet energy of the dopant or assisting dopant having the highest triplet energy in the light emitting layer from the viewpoint of promoting the generation of TADF in the light emitting layer without hindering it, Specifically, the triplet energy of the host material is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and still more preferably 0.1 eV or higher. Further, a compound having TADF activity may be used for the host material.

One type of host material may be sufficient as it, and a some combination may be sufficient as it. In the case of a plurality of combinations, a combination of a hole-transporting host material and an electron-transporting host material is preferable.

The polycyclic aromatic compound of the present invention can be preferably used as a host material. The polycyclic aromatic compound of the present invention may be used alone, may be used as a hole-transporting host material, or may be used as an electron-transporting host material. The polycyclic aromatic compound of the present invention is preferably used alone or as an electron-transporting host material.

On the other hand, it is also preferable to use a hole-transporting host material for the hole-transporting layer adjacent to the light-emitting layer, and to use an electron-transporting host material for the electron-transporting layer adjacent to the light-emitting layer. This is because carrier leakage and energy leakage from the light emitting layer to the adjacent layer are less likely to occur, and a highly efficient organic EL element can be obtained. The host material (hole-transporting host material) in the light emitting layer and the hole-transporting layer material may be the same or different. In addition, the host material (electron-transporting host material) in the light emitting layer and the material of the electron-transporting layer may be the same or different.

[Hole-transporting host material (HH)]

Examples of preferable hole-transporting host materials (HH) include, in addition to the polycyclic aromatic compounds of the present invention, compounds represented by formula (HH-1) and compounds having partial structures represented by formula (HH-1).

In formula (HH-1),

Q is >O, >S, or >N-A;

The carbon atom to which Q is bonded in each of the two phenyls in the formula (HH-1) and the adjacent carbon atom may be bonded to each other by L,

L is a single bond, >O, >S or >C(-A) ₂ ,

A is hydrogen, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and the two A's in >C(-A) ₂ are bonded to each other to form aryl, heteroaryl, cycloalkyl may form

When the hole-transporting host material contains the structure represented by formula (HH-1) as a partial structure, it may contain one partial structure, but it is also preferable to include two or more of these partial structures. When two or more are included, the two or more partial structures may be the same as or different from each other. Two or more partial structures may be bonded to each other by a single bond, may be bonded by sharing an arbitrary ring included in the partial structure, or may be bonded by condensing arbitrary rings included in the partial structure. The partial structure may further have a substituent selected from aryl, heteroaryl, diarylamino, or aryloxy.

The hole-transporting host material has at least one partial structure selected from the group consisting of a triarylamine structure, a carbazole ring, a dibenzofuran ring, and a dibenzothiophene ring, and a phenoxazine or phenothiazine-containing condensed polycyclic ring. It is preferable that it is a compound containing. The hole-transporting host material may contain one such partial structure, but it is also preferable to include two or more. When two or more are included, the two or more partial structures may be the same as or different from each other.

Specific examples of the hole-transporting host material include the following compounds.

Among the above, HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1-20 to HH-1-24 , HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92 and HH-1-106 to HH-1-108 are preferred.

[Electron transport host material (EH)]

Examples of the electron-transporting host material (EH) include, in addition to the polycyclic aromatic compound of the present invention, a compound represented by formula (EH-1) and a compound having a partial structure represented by formula (EH-1).

In formula (EH-1),

J is, each independently, =C(-A)- or =N-, and at least three Js are =C(-A)-;

Z is -O-, -S-, -C(=O)-, -P(=O)(-A)-, -P(=S)(-A)-, -N(-A)- , -B(-A)- or -S(=0) ₂ -,

The carbon atom to which Z is bonded and the A to which neighboring J and Z are bonded may be bonded to each other by L,

L is a single bond, >O, >S or >C(-A) ₂ ,

A is hydrogen, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, triarylsilyl, alkoxy or aryloxy, and the two A's in >C(-A) ₂ are bonded to each other to form aryl, hetero may form aryl or cycloalkyl;

When all J's are =C(-A)-, either A or Z has a heteroatom.

Description of A in formula (HH-1) for aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, triarylsilyl, alkoxy or aryloxy represented by A in formula (EH-1) can refer to. For aryls, heteroaryls, and cycloalkyls when two A's in formula (EH-1) combine with each other to form an aryl, heteroaryl, or cycloalkyl, see the description in formula (HH-1). can do.

When the electron transporting host material contains the structure represented by formula (EH-1) as a partial structure, it may contain one partial structure, but it is also preferable to include two or more of these partial structures. When two or more are included, the two or more partial structures may be the same as or different from each other. Two or more partial structures may be bonded to each other by a single bond, may be bonded by sharing an arbitrary ring included in the partial structure, or may be bonded by condensing arbitrary rings included in the partial structure. The partial structure may further have a substituent selected from aryl, heteroaryl, diarylamino, or aryloxy.

Specific examples of the electron-transporting host material include the following compounds.

　

　

As another preferable example of the electron-transporting host material (a compound having a partial structure represented by formula (EH-1)), a polycyclic aromatic compound represented by the following formula (EH-1b) or a compound represented by the following formula (EH-1b) Polymers of polycyclic aromatic compounds having a plurality of supporting structures are exemplified.

In formula (EH-1b),

R ¹ , R ² , R ³ , R ⁴ and R ⁵ (hereinafter also referred to as “R ¹ etc.”) are each independently hydrogen or a substituent selected from substituent group Z.

In Formula (EH-1b), X ¹ and X ² are each independently >NR (amine nitrogen), >O, >C(-R) ₂ , >S or >Se, and X ¹ and X ² together does not result in >C(-R) ₂ ,

R in >NR and >C(-R) ₂ is each independently hydrogen or a substituent selected from substituent group Z, and R in >NR and >C(-R) ₂ is each independently a linking group. Alternatively, it may be bonded to at least one of the a-rings, b-rings and c-rings by a single bond.

Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ and Y ⁶ (hereinafter also referred to as “Y ¹ etc.”) are each independently =C(-R)- or =N- (pyridinous nitrogen) , and at least one is =N-(pyridinic nitrogen),

R in =C(-R)- above is each independently hydrogen or a substituent selected from substituent group Z.

Adjacent groups among R ¹ , R ² , R ³ , R ⁴ and R ⁵ , and R in =C(-R)- as Y ¹ to ^{Y 6} are bonded to each other to form ring a, ring b and ring c An aryl ring or a heteroaryl ring may be formed together with at least one of the rings, and the formed ring may be substituted with at least one group selected from substituent group Z.

At least one hydrogen in the compound and structure represented by formula (EH-1b) may be substituted with cyano, halogen or deuterium.

In the formula (EH-1b), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are all hydrogen, or both R ³ and R ⁴ are hydrogen, and R ¹ , R ² and R ⁵ are also It is preferable that any one or more selected from the group which consists of is a substituent other than hydrogen, and others are hydrogen. As the substituent, aryl which may be substituted with alkyl, alkyl or heteroaryl, heteroaryl which may be substituted with alkyl or aryl, or diarylamino which may be substituted with alkyl or aryl is preferable. At this time, the alkyl is preferably an alkyl having 1 to 6 carbon atoms (methyl, t-butyl, etc.), the aryl is preferably phenyl or biphenyl, and the heteroaryl is triazinyl, carbazolyl (2-carbazolyl , 3-carbazolyl, 9-carbazolyl, etc.), pyrimidinyl, pyridinyl, dibenzofuranyl or dibenzothienyl are preferred. Specific examples include phenyl, biphenyl, diphenyltriazinyl, carbazolyltriazinyl, monophenylpyrimidinyl, diphenylpyrimidinyl, carbazolyltriazinyl, pyridinyl, dibenzofuranyl and dibenzothienyl. can be heard

Y ¹ and the like are each independently =C(-R)- or =N-, and at least one of them is =N-. Any of Y ¹ to ^{Y 6} may be =N-. Preferably, Y ¹ and Y ⁶ are =N- (a ring is a pyrimidine ring), Y ¹ and Y ⁶ are =N- (a ring is a pyridine ring), Y ² and Y ⁵ are =N- (b ring and ring c is pyridine ring), Y ³ and Y ⁴ are =N- (ring b and c are pyridine rings), Y ² to ^{Y 5} are =N- (ring b and c are pyrimidine rings), Y ¹ , Y ³ , Y ⁴ and Y ⁶ are =N- (ring a is a pyrimidine ring, ring b and ring c are a pyridine ring), Y ¹ , Y ² , Y ⁵ and Y ⁶ are =N- (ring a is a pyrimidine ring, ring b and c ring is a pyridine ring), Y ¹ to ^{Y 6} is =N- (ring a, b and c are pyrimidine rings), and Y ² or Y ⁵ is =N- (ring b or c is a pyridine ring).

Further, in addition to the arrangement relationship of =N- above, it is preferable that X ¹ and X ² are >0, and a polycyclic aromatic compound containing a partial structure represented by any one of the following formulas is preferable.

In particular, a polycyclic aromatic compound having a partial structure represented by formula (EH-1b-N1) has higher E _S1 , higher E _T1 , and smaller ΔE _S1T1 than a structure without N.

Specific examples of the polycyclic aromatic compound represented by formula (EH-1b) are shown below.

Among the above, EH-1-1 to EH-1-4, EH-1-10, EH-1-21 to EH-1-25, EH-1-32, EH-1-33, EH-1-51 ∼EH-1-59, EH-1-61, EH-1-66, EH-1-68, EH-1-71, EH-1-72, EH-1-90, EH-1-100, EH -1-101, EH-1-104, EH-1-115, EH-1-117, EH-1-120, EH-1-122, EH-1-123, EH-1-127 to EH-1 -130 is preferred.

[Combination of hole-transporting host material and electron-transporting host material]

A combination of the hole-transporting host material and the electron-transporting host material is selected according to the HOMO, LUMO, and triplet excitation energy of the hole-transporting host material, the electron-transporting host material, and the dopant material.

Regarding HOMO and LUMO, the HOMO (HH) of the hole-transporting host material is shallower than the HOMO (EH) of the electron-transporting host material, and the LUMO (EH) of the electron-transporting host material is deeper than the LUMO (HH) of the hole-transporting host material. Select a combination, more specifically, a combination in which HOMO(HH) is 0.10 eV or more shallower than HOMO(EH), LUMO(HH) is 0.10 eV or more deeper than HOMO(EH), and HOMO(HH) is HOMO A combination in which 0.20eV or more shallow than (EH), LUMO(HH) is 0.20eV or more deeper than HOMO(EH) is more preferable, HOMO(HH) is 0.25eV or more shallower than HOMO(EH), and LUMO(HH) is HOMO A combination at least 0.25 eV deeper than (EH) is more preferable.

The hole-transporting host material and the electron-transporting host material may be a combination that forms an association called an exciplex. It is generally known that exciplex is easy to form between a material having a relatively deep LUMO level and a material having a shallow HOMO level. The interaction of the hole-transporting host material and the electron-transporting host material, specifically, whether or not an exciplex is formed is determined by forming a monolayer film composed of the hole-transporting host material and the electron-transporting host material under the same conditions as the formation conditions of the light emitting layer, and emitting light. It can be judged by measuring the spectrum (fluorescence and phosphorescence spectrum) and comparing the obtained emission spectrum with the emission spectrum exhibited by each of the hole-transporting host material and the electron-transporting host material alone. The spectrum of the mixed film containing the hole-transporting host material and the electron-transporting host material can be determined by showing an emission wavelength different from both the spectrum of the film of the hole-transporting host material and the spectrum of the film of the electron-transporting host material. Specifically, what is necessary is just to use the indicator as the peak wavelengths of the spectra differing by 10 nm or more.

Specific examples of combinations of a hole-transporting host material and an electron-transporting host material that do not form an exciplex include the following combinations. In order to satisfy the above physical property values of HOMO, LUMO and excitation triplet energy, in the hole transporting host material, carbazole, dibenzofuran, dibenzothiophene, triarylamine, indolocarbazole and benzoxazinophenoxazine A compound having as a partial structure is preferable, a compound having carbazole, dibenzofuran and dibenzothiophene as a partial structure is more preferable, and a compound having carbazole as a partial structure is even more preferable. Similarly, in the electron-transporting host material, compounds having pyridine, triazine, phosphine oxide, benzofuropyridine and dibenzoxacillin as partial structures are preferred, and triazine, phosphine oxide, benzofuropyridine and dibenzooxa A compound having silin as a partial structure is more preferred, and a compound having triazine is even more preferred.

More specifically, the hole-transporting host material is HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1 -20 to HH-1-24, HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92 and HH-1-106 to HH-1-108 It is preferably selected from the group consisting of, and the electron transporting host material is EH-1-1 to EH-1-4, EH-1-10, EH-1-21 to EH-1-25, EH-1- 32, EH-1-33, EH-1-51 to EH-1-59, EH-1-61, EH-1-71, EH-1-72, EH-1-90, EH-1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127 to EH-1-130 It is preferable to be selected from the group. Preferable examples of combinations include compound HH-1-1 and compound EH-1-22, compound HH-1-1 and compound EH-1-23, compound HH-1-1 and compound EH-1-24, compound HH- 1-2 and compound EH-1-22, compound HH-1-2 and compound EH-1-23, compound HH-1-2 and compound EH-1-24, or compound HH-1-1 and compound EH- 1-128 may be cited.

Specific examples of combinations of a hole-transporting host material and an electron-transporting host material forming an exciplex include the following combinations. In order to satisfy the above physical property values of HOMO, LUMO and excitation triplet energy, compounds having carbazole, triarylamine, indolocarbazole and benzoxazinophenoxazine as partial structures are preferred for the hole-transporting host material, , compounds having triarylamine, indolocarbazole and benzoxazinophenoxazine as partial structures are more preferred, and compounds having triarylamine as partial structures are even more preferred. Similarly, in the electron-transporting host material, compounds having pyridine, triazine, phosphine oxide, and benzofuropyridine as partial structures are preferred, and triazine, phosphine oxide, benzofuropyridine, and dibenzoxacillin as partial structures. Compounds having phosphine oxide and triazine are more preferred.

More specifically, the hole transporting host material is HH-1-1, HH-1-2, HH-1-11, HH-1-12, HH-1-17, HH-1-18, HH-1 It is preferably selected from the group consisting of -23 and HH-1-24, and the electron transporting host material is EH-1-1 to EH-1-4, EH-1-21 to EH-1-25, EH- 1-51 to EH-1-57, EH-1-59, EH-1-66, EH-1-68, EH-1-90, EH-1-100, EH-1-101, EH-1- 104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127 to EH-1-130. Preferable examples of combinations include compound HH-1-1 and compound EH-1-21, compound HH-1-2 and compound EH-1-21, compound HH-1-12 and compound EH-1-117, compound HH- 1-1 and compound EH-1-130, compound HH-1-33 and compound EH-1-117, compound HH-1-48 and compound EH-1-117 or compound HH-1-49 and compound EH-1 -117 can be heard.

In addition, for a specific combination of a hole-transporting host material and an electron-transporting host material, Organic Electronics 66 (2019) 227-24, Advanced. Functional Materals 25 (2015) 361-366., Advanced Materials 26 (2014) 4730-4734., ACS Applied Materials and Interfaces 8 (2016) 32984-32991., ACS Applied Materals and Interfaces 2016, 8, 9806-9810, ACS Applied Materials and Interfaces 2016, 8, 32984-32991, Journal of Materials Chemisty C, 2018, 6, 8784-8792, Angewante Chemie International Edition. 2018, 57, 12380-12384, Advanced Functional Materials, 24, 2014, 3970, Advanced Materials, 26, 2014, 5684, and Synthetic Metals, 201, 2015, 49 may be referred to.

<Dopant material>

As the dopant material, a known compound can be used, and it can be selected from various materials depending on the desired emission color. Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, and benzothiazole derivatives, benzoimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, Tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (Japanese Patent Laid-Open No. 1-245087), bisstyrylarylene derivatives (Japanese Patent Laid-Open No. 2 -247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenyl isobenzofuran, dimethyl isobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)iso Isobenzofuran derivatives such as benzofuran and phenylisobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7 -Coumarin derivatives such as acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzoimidazolylcoumarin derivatives, and 3-benzooxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, Quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrimethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, bioranthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives, and the like.

As the emitting dopant material, it is also preferable to use a polycyclic aromatic compound containing boron described in paragraphs 0097 to 0269 of International Publication No. 2015/102118, International Publication No. 2020/162600, and Japanese Patent Application Publication No. 2021-077890 and the like. . The polycyclic aromatic compound having a boron atom may be a phosphor or a TADF material (heat-activated delayed phosphor). The polycyclic aromatic compound having a boron atom is preferably a blue light emitting compound.

As a preferable example of the polycyclic aromatic compound containing boron, the compound represented by following formula (12), formula (13), or formula (14) is mentioned.

A ring, B ring, C ring, and D ring are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring;

Y is B (boron);

X ¹ , X ² , X ³ and X ⁴ are each independently >O, >NR, >S or >Se, wherein R of >NR is substituted or unsubstituted aryl, substituted or unsubstituted hetero aryl or substituted or unsubstituted alkyl, and R in >NR may be bonded to the A ring, B ring, C ring and/or D ring by a linking group or a single bond;

R ¹ and R ² are each independently hydrogen, alkyl having 1 to 6 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms); ,

Z ¹ and Z ² are each independently any one substituent selected from substituent group Z, Z ¹ may bond to the A ring through a linking group or single bond, and Z ² bonds to the C ring through a linking group or single bond. you can do it, and

At least one hydrogen in the compound represented by formula (12) may be substituted with cyano, halogen or deuterium.

In the A ring, B ring, C ring and D ring of formula (12), as the substituent when the aryl ring or heteroaryl ring is substituted, and Z ¹ , Z ² , a substituent selected from substituent group Z is exemplified. there is.

X ¹ , X ² , X ³ and X ⁴ in formula (12) are each independently >O, >NR, >S or >Se, and R in >NR is each independently 6 carbon atoms It is aryl of -12, heteroaryl of 2-15 carbon atoms, cycloalkyl of 3-12 carbon atoms, or alkyl of 1-6 carbon atoms.

In the compound represented by formula (12), from the viewpoint of high TADF property, it is preferable that Z ¹ and Z ² are diphenylamino which may have a substituent or N-carbazolyl which may have a substituent, and has a substituent It is more preferable that it is also diphenylamino. As diphenylamino which may have a substituent, unsubstituted diphenylamino or diphenylamino having at least one alkyl of 1 to 4 carbon atoms is preferable, and unsubstituted diphenylamino or m-position or o relative to N Diphenylamino having at least one methyl at the position is more preferred. From the viewpoint of the ease of synthesis and emission wavelength, the aryl or heteroaryl rings in the A, B, C and D rings have no substituents other than Z ¹ and Z ² , or have only alkyl of 1 to 6 carbon atoms. It is preferable to have as an external substituent, and it is more preferable to have no substituent other than Z ¹ and Z ² .

The example of the compound represented by Formula (12) is shown below.

In formulas (13) and (14),

A ¹¹ ring, A ²¹ ring, A ³¹ ring, B ¹¹ ring, B ²¹ ring, C ¹¹ ring, and C ³¹ ring are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. ,

Y ¹¹ , Y ²¹ , Y ³¹ are B (boron);

X ¹¹ , X ¹² , X ²¹ , X ²² , X ³¹ , and X ³² are each independently >O, >NR, >S, or >Se, wherein R in >NR is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl or substituted or unsubstituted alkyl, and R in >NR is A ¹¹ ring, A ²¹ ring, A ³¹ ring, B ¹¹ ring, B ²¹ ring by a linking group or a single bond. , may be bonded to the C ¹¹ ring, and/or the C ³¹ ring;

At least one hydrogen in the compounds represented by formulas (13) and (14) may be substituted with cyano, halogen or deuterium.

The aryl ring or heteroaryl ring in the A ¹¹ ring, the A ²¹ ring, the A ³¹ ring, the B ¹¹ ring, the B ²¹ ring, the C ¹¹ ring, and the C ³¹ ring in Formulas (13) and (14) is substituted. As the substituent and Z ¹ , Z ² when present, a substituent selected from the substituent group Z is exemplified.

X ¹¹ , X ¹² , X ²¹ , X ²² , X ³¹ , and X ³² in Formulas (13) and (14) are each independently >O, >NR, >S, or >Se, and the above R in >NR is each independently an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, or an alkyl having 1 to 6 carbon atoms.

Examples of compounds represented by formula (13) or formula (14) are shown below.

<Heat activated delayed phosphor (assisting dopant)>

"Thermally activated delayed phosphor" is a phosphor capable of absorbing thermal energy to cause inverse intersystem crossing from the lowest triplet excited state to the lowest singlet excited state, and radiatively deactivated from the lowest singlet excited state to emit delayed fluorescence. means compound. However, "heat-activated delayed fluorescence" includes high-order triplet excitation in the excitation process from the lowest triplet excited state to the lowest singlet excited state. For example, a paper by Monkmans, Durham University (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038/ncomms 13680), a paper by Hosokai et al., Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci.Adv. 2017; 3 :e1603282), a thesis by scholars of Kyoto University (Scientific Reports, 7:4820, DOI:10.1038/s41598-017-05007-7), as well as a conference presentation by scholars of Kyoto University (The Chemical Society of Japan 98th Spring Banquet) , Publication No.: 2I4-15, Mechanism of Highly Efficient Luminescence in Organic Electroluminescence Using DABNA as a Light-Emitting Molecule, Graduate School of Engineering, Kyoto University), and the like. In the present invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300 K, a slow fluorescence component is observed, and the target compound is determined to be a "heat-activated delayed phosphor". Here, the slow fluorescence component refers to a fluorescence lifetime of 0.1 μsec or more. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measuring device (C11367-01 manufactured by Hamamatsu Photonics Co., Ltd.).

In the following description, an organic electroluminescent element using a thermally activated delayed phosphor as an assisting dopant is sometimes referred to as a "TAF element" (TADF Assisting Fluorescence element).

The "host compound" in a TAF element means a compound whose lowest excitation singlet energy level obtained from the shoulder of the short wavelength side of the peak of the fluorescence spectrum is higher than that of the thermally activated delayed phosphor as an assisting dopant and the emitting dopant. .

FIG. 2 shows an energy level diagram of a light emitting layer of a TAF device using a general fluorescent dopant as an emitting dopant (ED). In the figure, the energy level of the ground state of the host is E(1, G), the lowest excitation singlet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the host is E(1, S, Sh), and the phosphorescence spectrum of the host The lowest excitation triplet energy level obtained from the shoulder on the short wavelength side is E(1, T, Sh), the ground state energy level of the assisting dopant is E(2, G), and the shoulder on the short wavelength side of the fluorescence spectrum of the assisting dopant The lowest excitation singlet energy level obtained from E(2, S, Sh), the lowest excitation triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the assisting dopant is E(2, T, Sh), The energy level of the ground state of the ting dopant is E(3, G), the lowest excitation singlet energy level obtained from the shoulder of the short wavelength side of the fluorescence spectrum of the emitting dopant is E(3, S, Sh), The lowest excitation triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum is E(3, T, Sh), the hole is h+, the electron is e-, and the fluorescence resonance energy transfer is FRET (Fluorescence Resonance Energy Transfer). In the TAF device, when a general fluorescent dopant is used as the emitting dopant (ED), energy upconverted from the assisting dopant moves to the lowest excitation singlet energy level E(3, S, Sh) of the assisting dopant and emits light. do. However, a portion of the lowest excitation triplet energy level E(2, T, Sh) on the assisting dopant moves to the excitation triplet energy level E(3, T, Sh) of the emitting dopant, or the lowest excitation on the emitting dopant. Intersystem crossing occurs from the singlet energy level E(3, S, Sh) to the lowest excitation triplet energy level E(3, T, Sh), and then thermally to the ground state E(3, G). to be inactive A part of the energy is not used for light emission through this path, and energy is wasted.

In contrast, in the organic EL device of the present embodiment, energy transferred from the assisting dopant to the emitting dopant can be efficiently used for light emission, and thus high light emission efficiency can be realized. This is estimated to be based on the following light emission mechanism.

A preferable energy relationship in the organic electroluminescent device of the present embodiment is shown in FIG. 3 . In the organic electroluminescent device of this embodiment, a compound having a boron atom as an emitter dopant has a high lowest triplet excitation energy level E(3, T, Sh). Because of this, even when the excitation singlet energy upconverted in the assisting dopant intersects, for example, to the lowest excitation triplet energy level E(3, T, Sh) in the emitting dopant, it is upconverted on the emitting dopant. It is converted or recovered to the lowest excitation triplet energy level E(2, T, Sh) on the assisting dopant (thermally activated delayed phosphor). Therefore, the generated excitation energy can be used for light emission without waste. In addition, by dividing into two types of molecules capable of improving the function of upconversion and light emission, respectively, it is expected that the residence time of high energy is reduced and the burden on the compound is reduced.

In this embodiment, known host compounds can be used, and examples thereof include compounds having at least one of a carbazole ring and a furan ring, and among them, at least one of furanyl and carbazolyl, and an aryl It is preferable to use a compound in which at least one of ene and heteroarylene is bonded. As a specific example, mCP, mCBP, etc. are mentioned.

The lowest excitation triplet energy level E (1, T, Sh) determined from the shoulder of the short wavelength side of the peak of the phosphorescence spectrum of the host compound is the highest in the light emitting layer from the viewpoint of promoting the generation of TADF in the light emitting layer without hindering it. It is preferably higher than the lowest triplet excitation energy levels E(2, T, Sh) and E(3, T, Sh) of the emitting dopant or assisting dopant having the highest lowest excitation triplet energy level, specifically, , The lowest excitation triplet energy level E(1, T, Sh) of the host compound is preferably 0.01eV or more higher than E(2, T, Sh), E(3, T, Sh), and is 0.03eV or more A high value is more preferred, and a value higher than 0.1 eV is still more preferred. Further, a compound having TADF activity may be used as the host compound.

The thermally activated delayed phosphor (TADF compound) used in the TAF element uses an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to achieve HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied It is preferable to be a donor-acceptor type thermally activated delayed phosphor (D-A type TADF compound) designed to localize molecular orbitals and cause efficient reverse intersystem crossing.

Here, in the present specification, "electron-donating substituent" (donor) means a substituent and partial structure in which HOMO is localized in a heat-activated delayed phosphor molecule, and "electron-accepting substituent" (acceptor) means a heat It shall mean the substituent and partial structure in which LUMO is localized in active type delayed phosphor molecule.

In general, a thermally activated delayed phosphor using a donor or acceptor has a large spin-orbit coupling (SOC) due to its structure, and at the same time, the exchange interaction between HOMO and LUMO is small and ΔE _S1T1 is small, so, Very fast inverse interphase crossing velocities are obtained. On the other hand, thermally activated delayed phosphors using a donor or acceptor have a large structural relaxation in the excited state (since the stable structure is different between the ground state and the excited state in some molecules, it is changed from the ground state to the excited state by external stimulation). When conversion occurs, the structure is then changed to a stable structure in an excited state), providing a wide luminescence spectrum, so there is a possibility of reducing color purity when used as a luminescent material. However, high color purity can be obtained by using a thermally activated delayed phosphor using a donor or acceptor as an assisting dopant together with an appropriate emitting dopant such as a compound represented by Formula (12), Formula (13) or Formula (14). can provide.

As the thermally activated delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are bonded directly or through a spacer can be used. As the electron-donating group (donor structure) and electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 can be used As the donor structure, carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, Phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis (tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro- indenoacridine and diphenyl-dihydrodibenzoazacillin; and the like. As the acceptor structure, sulfonyldibenzene, benzophenone, phenylenebis (phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole , oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzooxazole, benzobis(oxazole), quinoline, benzoimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide , dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorenedicarbonitrile, triphenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyridine midine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthenedioxide, thianthrenetetraoxide and tris(dimethylphenyl)borane. Particularly, the compound having thermally activated delayed fluorescence in the TAF element has, as a partial structure, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isop It is preferably a compound having at least one selected from talonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone.

The compound used as the assisting dopant of the light emitting layer in the TAF element is a thermally activated delayed phosphor, and it is preferable that the emission spectrum overlaps at least partially with the absorption peak of the emitting dopant.

<Phosphorescent material (assisting dopant)>

In the light emitting layer, you may use a phosphorescent material as an assisting dopant. Phosphorescent materials utilize intramolecular spin-orbit interactions (heavy atom effect) by metal atoms to obtain light emission from triplets. As such a phosphorescent material, a luminescent metal complex can be used, for example. Examples of the luminescent metal complex include compounds represented by the following formula (B-1) and the following formula (B-2).

In formula (B-1), M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu, n is an integer of 1 to 3, and "X-Y" are each independently a bidentate ligand.

In formula (B-2), M is at least one selected from the group consisting of Pt, Re and Cu, and "W-X-Y-Z" is a tetradentate ligand.

In the formula (B-1), from the viewpoint of efficiency and lifetime, M is preferably Ir, and n is preferably 3.

In Formula (B-2), M is preferably Pt from the viewpoint of efficiency and lifetime.

The ligand (X-Y) in the formula (B-1) has at least one ligand selected from the group consisting of the following. The ligand (W-X-Y-Z) in the formula (B-2) has at least one ligand selected from the group consisting of the following as a part.

during the ceremony,

--- in combination with the central metal M,

Y is, each independently, BR _e , NR _e , PR _e , O, S, Se, C=O, S=O, SO2, CR _e R _f , SiR _e R _f , or GeR _e R _f ;

Aromatic carbons C-H in the ring may each independently be substituted with N,

R _e and R _f may be optionally condensed or bonded to form a ring,

R _a , R _b , R _c , and R _d may each independently be unsubstituted or substituted by 1 to the maximum number of substitutions;

R _a , R _b , R _c , R _d , R _e , and R _f are each, independently, hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl , cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or a combination thereof,

However, arbitrary two adjacent substituents in R _a , R _b , R _c , and R _d may form a ring by condensation or bonding, or may form a multidentate ligand.

Examples of the compound represented by formula (B-1) include Ir(ppy) ₃ , Ir(ppy) ₂ (acac), Ir(mppy) ₃ , Ir(PPy) ₂ (m-bppy), BtpIr( acac), Ir(btp) ₂ (acac), Ir(2-phq) ₃ , Hex-Ir(phq) ₃ , Ir(fbi) ₂ (acac), fac-Tris(2-(3-p-xylyl) phenyl)pyridine iridium(III), Eu(dbm) ₃ (Phen), Ir(piq) ₃ , Ir(piq) ₂ (acac), Ir(Fliq) ₂ (acac), Ir(Flq) ₂ (acac), Ru(dtb-bpy) ₃ 2(PF ₆ ), Ir(2-phq) ₃ , Ir(BT) ₂ (acac), Ir(DMP) ₃ , Ir(Mphq) ₃ IR(phq) ₂ tpy, fac -Ir(ppy) ₂ Pc, Ir(dp)PQ ₂ , Ir(Dpm)(Piq) ₂ , Hex-Ir(piq) ₂ (acac), Hex-Ir(piq) ₃ , Ir(dmpq) ₃ , Ir (dmpq) ₂ (acac), FPQIrpic, and the like.

As a compound represented by Formula (B-1), the following formula is mentioned, for example in others.

Further, Japanese Unexamined Patent Publication No. 2006-089398, Japanese Unexamined Patent Publication No. 2006-080419, Japanese Unexamined Patent Publication No. 2005-298483, Japanese Unexamined Patent Publication No. 2005-097263, and Japanese Unexamined Patent Publication No. 2004-111379, US Patent Iridium complexes described in the specification of Patent Application Publication No. 2019/0051845, etc., or Advanced Materials, 26:7116-7121, NPG Asia Materials 13, 53 (2021), Applied Physics Letters, 117, 253301 (2020), Light-Emitting Diode- The platinum complex described in An Outlook On the Empirical Features and Its Recent Technological Advancements, Chapter 5 may be used.

<Electron Injection Layer and Electron Transport Layer in Organic Electroluminescent Device>

The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light emitting layer 105 or into the electron transport layer 106 . The electron transport layer 106 serves to efficiently transport electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105 . The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or more electron transport/injection materials, or a mixture of an electron transport/injection material and a polymeric binder.

The electron injection/transport layer is a layer responsible for injecting electrons from the cathode and transporting the electrons, and preferably has high electron injection efficiency and efficiently transports the injected electrons. For this purpose, it is preferable to use a material that has high electron affinity, high electron mobility, and excellent stability, and is unlikely to generate trap impurities during production and use. However, in the case of considering the transport balance of holes and electrons, when the role of efficiently preventing the flow of holes from the anode to the cathode side without recombination is mainly performed, even if the electron transport capacity is not so high, the luminous efficiency is improved. The effect is equivalent to that of a material having a high electron transport ability. Therefore, the electron injection/transport layer in the present embodiment may also include a function of a layer capable of effectively blocking the movement of holes.

As the material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a compound conventionally used as an electron transport compound in photoconductive materials, an electron injection layer and an electron transport layer of an organic EL device. It can be used by selecting it arbitrarily from known compounds in use. It is also preferable to use the polycyclic aromatic compound of the present invention as a material for an electron transport layer.

As the material used for the electron transport layer or the electron injection layer, compounds comprising an aromatic ring or heteroaromatic ring composed of at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, pyrrole derivatives and condensed ring derivatives thereof; It is preferable to contain at least 1 sort(s) selected from metal complexes which have electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives , quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Although these materials are used alone, you may mix and use them with other materials.

In addition, as specific examples of other electron transfer compounds, pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone Derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N- naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of auxin derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazoles compounds, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9' -spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives , Oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis (2,2': 6', 2"-terpyridin-4'-yl) benzene, etc.), naphthyridine derivatives ( bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc. can be heard

In addition, metal complexes having electron-accepting nitrogen can also be used, for example, quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes. and benzoquinoline metal complexes.

The above materials are used alone, but may be used in combination with other materials.

Among the above materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, Phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

The electron transport layer or electron injection layer may further contain a substance capable of reducing a material forming the electron transport layer or electron injection layer. As long as this reducing substance has a certain reducing property, various substances are used, for example, alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, and alkaline earths. At least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV copper), Rb (2.16 eV copper) or Cs (1.95 eV copper), Ca (2.9 eV copper), and Sr (2.0 eV copper). to 2.5 eV) or an alkaline earth metal such as Ba (copper 2.52 eV), and a substance having a work function of 2.9 eV or less is particularly preferred. Among these, a more preferable reducing substance is an alkali metal of K, Rb or Cs, even more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the material forming the electron transport layer or the electron injection layer can improve the light emission luminance and lengthen the lifetime of the organic EL device. In addition, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and A combination of Na and K is preferred. By including Cs, reducing ability can be exhibited efficiently, and addition to the material forming the electron transport layer or electron injection layer can improve the luminescence brightness and lengthen the lifetime of the organic EL device.

<Cathode in organic electroluminescence device>

The cathode 108 serves to inject electrons into the light emitting layer 105 through the electron injection layer 107 and the electron transport layer 106 .

The material forming the cathode 108 is not particularly limited as long as it is a material capable of efficiently injecting electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among them, metals or alloys thereof (magnesium-silver alloy, magnesium- aluminum-lithium alloys such as indium alloys and lithium fluoride/aluminum); In order to improve device characteristics by increasing electron injection efficiency, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in air in many cases. In order to improve this point, a method is known in which, for example, an organic layer is doped with a small amount of lithium, cesium or magnesium to use an electrode having high stability. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

Furthermore, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbons for electrode protection Preferred examples include laminating a polymeric compound or the like. Methods for producing these electrodes are not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating and coating.

<Method of manufacturing organic electroluminescence device>

For each layer constituting the organic EL device, the material constituting each layer is formed into a thin film by a method such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination method, printing method, spin coating method, casting method, or coating method. By doing so, it can be formed. The film thickness of each layer formed in this way is not particularly limited and can be appropriately set depending on the nature of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. In the case of thinning using a vapor deposition method, the deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. Deposition conditions are generally boat heating temperature +50 to +400 ° C, vacuum degree 10 ^-6 to ^{10 -3} Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300 ° C, film thickness 2 nm to 5 μm. It is desirable to set appropriately within the range.

In the case of applying a direct current voltage to the organic EL element obtained in this way, the anode may be applied with + and the cathode as the polarity, and when a voltage of about 2 to 40 V is applied, the transparent or translucent electrode side (anode or cathode) , and both) can observe luminescence. In addition, this organic EL element emits light even when a pulse current or an alternating current is applied. In addition, the waveform of the alternating current to apply may be arbitrary.

Next, as an example of a method for manufacturing an organic EL device, a method for manufacturing an organic EL device composed of an anode/a hole injection layer/a hole transport layer/a light emitting layer composed of a host material and a dopant material/an electron transport layer/an electron injection layer/cathode Explain.

<Deposition method>

After fabricating an anode by forming a thin film of anode material on a suitable substrate by vapor deposition or the like, thin films of a hole injection layer and a hole transport layer are formed on the anode. A host material and a dopant material are co-evaporated thereon to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a material for the cathode is formed by a vapor deposition method or the like to form a cathode. An organic EL element made of is obtained. In addition, in fabricating the organic EL device described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer and anode in this order.

<Wet film forming method>

The wet film forming method is performed by preparing a low-molecular compound capable of forming each organic layer of an organic EL element as a liquid composition for forming an organic layer, and using the same. When there is no suitable organic solvent for dissolving the low molecular weight compound, a reactive compound obtained by substituting a reactive substituent in the low molecular weight compound and a composition for forming an organic layer from a high molecular compound polymerized together with other monomers having a soluble function or a main chain polymer, etc. you can prepare

In the wet film forming method, generally, a coating film is formed by passing through an application step of applying a composition for forming an organic layer to a substrate and a drying step of removing a solvent from the applied composition for forming an organic layer. When the polymer compound has a cross-linkable substituent (also referred to as a cross-linkable polymer compound), it is further cross-linked in this drying step to form a polymer cross-linked body. Depending on the difference in the coating process, the spin coat method uses a spin coater, the slit coat method uses a slit coater, and the gravure offset, reverse offset, flexographic printing, and inkjet printers are used for the plate method. The method of doing this is called the inkjet method, and the method of spraying in the form of mist is called the spray method. The drying process includes methods such as air drying, heating, and drying under reduced pressure. The drying step may be performed only once, or may be performed a plurality of times using different methods and conditions. In addition, you may use other methods together, such as baking under reduced pressure, for example.

The wet film forming method is a film forming method using a solution, and includes, for example, some printing methods (inkjet method), a spin coat method, a cast method, a coating method, and the like. Unlike the vacuum deposition method, the wet film formation method does not require the use of an expensive vacuum deposition apparatus and can form a film under atmospheric pressure. In addition, the wet film forming method enables large-area and continuous production, leading to reduction in manufacturing cost.

On the other hand, when compared with the vacuum evaporation method, the wet film formation method may be difficult to laminate. When a multilayer film is produced using a wet film forming method, it is necessary to prevent dissolution of the lower layer by the composition of the upper layer, so a composition with controlled solubility, cross-linking of the lower layer and orthogonal solvent (solvent that does not dissolve in each other), etc. this is spoken However, even if these techniques are used, there are cases where it is difficult to use the wet film formation method for coating all films.

Therefore, generally, a method of fabricating an organic EL device by using a wet film forming method for only a few layers and vacuum evaporation is employed for the rest.

For example, a procedure for fabricating an organic EL device by partially applying a wet film forming method is shown below.

(Procedure 1) Film formation by vacuum evaporation of the anode

(Procedure 2) Formation of a composition for forming a hole injection layer containing a material for a hole injection layer by a wet film forming method

(Procedure 3) Formation of a composition for forming a hole transport layer containing a material for a hole transport layer by a wet film forming method

(Procedure 4) Formation of a composition for forming a light emitting layer containing a host material and a dopant material by a wet film forming method

(Procedure 5) Film formation of electron transport layer by vacuum deposition method

(Procedure 6) Film formation of electron injection layer by vacuum deposition method

(Procedure 7) Film formation by vacuum evaporation of cathode

By passing through this sequence, an organic EL device composed of anode/hole injection layer/hole transport layer/light emitting layer composed of host material and dopant material/electron transport layer/electron injection layer/cathode is obtained.

Of course, the electron transport layer and the electron injection layer may also be formed by a wet film forming method using a composition for layer formation containing a material for an electron transport layer and a material for an electron injection layer, respectively. At this time, it is preferable to use a means for preventing dissolution of the lower light emitting layer or a means for forming a film from the cathode side in the opposite order to the above procedure.

<Other Tabernacling Methods>

A laser heating drawing method (LITI) can be used for film formation of the composition for forming an organic layer. LITI is a method of heating and depositing a compound attached to a substrate with a laser, and a composition for forming an organic layer can be used for a material applied to the substrate.

<Random process>

Appropriate treatment steps, washing steps, and drying steps may be suitably incorporated before and after each step of film formation. Examples of the treatment step include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, washing treatment using an appropriate solvent, heat treatment, and the like. In addition, a series of steps for producing a bank are also mentioned.

A photolithography technique can be used for fabrication of the bank. As a bank material for which photolithography can be used, a positive type resist material and a negative type resist material can be used. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, a permanent resist material may be used.

<Composition for Forming Organic Layer Used in Wet Film Formation>

A composition for forming an organic layer is obtained by dissolving a low-molecular compound capable of forming each organic layer of an organic EL device or a high-molecular compound obtained by polymerizing the low-molecular compound in an organic solvent. For example, a composition for forming a light emitting layer includes at least one polycyclic aromatic compound (or a polymer compound thereof) as a dopant material as a first component, at least one host material as a second component, and at least one as a third component. Contains a species of organic solvent. The first component functions as a dopant component of the light emitting layer obtained from the composition, and the second component functions as a host component of the light emitting layer. The third component functions as a solvent for dissolving the first and second components in the composition, and upon application imparts a smooth and uniform surface shape by the controlled evaporation rate of the third component itself.

<Organic Solvent>

The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve film formability, presence or absence of defects in the coating film, surface roughness, and smoothness. Further, in the case of film formation using the inkjet method, the meniscus stability in the pinhole of the inkjet head can be controlled to control and improve ejection properties. In addition, by controlling the drying speed of the film and the orientation of the derivative molecules, it is possible to improve the electrical characteristics, light-emitting characteristics, efficiency, and lifetime of an organic EL device having an organic layer obtained from the composition for forming an organic layer.

After film formation, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. In the case of heating, from the viewpoint of improving coating film formability, it is preferable to perform heating at a glass transition temperature (Tg) of at least one of the solutes +30°C or lower. Further, from the viewpoint of reducing the residual solvent, it is preferable to heat the glass transition point (Tg) of at least one of the solutes to -30°C or higher. Since the film is thin even when the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed. Moreover, drying may be performed multiple times at different temperatures, or a plurality of drying methods may be used in combination.

(2) Specific examples of organic solvents

Examples of organic solvents used in the composition for forming an organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and Fluorine-type solvent etc. are mentioned, but it is not limited to this. In addition, a solvent may be used singly or may be mixed.

<Optional ingredients>

The composition for forming an organic layer may contain arbitrary components within a range that does not impair its properties. As an arbitrary component, a binder, surfactant, etc. are mentioned.

<Composition and physical properties of composition for forming organic layer>

The content of each component in the composition for forming an organic layer determines the good solubility, storage stability and film-forming properties of each component in the composition for forming an organic layer, the quality of a coating film obtained from the composition for forming an organic layer, and the inkjet method. It is determined in consideration of the good ejection properties in the case of use, and the good electrical characteristics, light emitting characteristics, efficiency, and lifetime of an organic EL device having an organic layer produced using the composition.

The composition for forming an organic layer can be prepared by appropriately selecting and performing stirring, mixing, heating, cooling, dissolution, dispersion, etc. of the above-mentioned components by a known method. After preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, and inert gas replacement/encapsulation treatment may be appropriately selected and performed.

<Application example of organic electroluminescence device>

INDUSTRIAL APPLICABILITY The present invention can also be applied to a display device including an organic EL element or a lighting device including an organic EL element.

A display device or lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element according to the present embodiment to a known drive device, and known DC drive, pulse drive, AC drive, etc. It can be driven by appropriately using the driving method of .

Examples of the display device include a panel display such as a color flat panel display, a flexible display such as a flexible color organic electroluminescent (EL) display, and the like (eg, Japanese Patent Laid-Open No. 10-335066, Japanese Unexamined Patent Publication No. 2003-321546, Japanese Unexamined Patent Publication No. 2004-281086, etc.). In addition, as a display method of a display, a matrix method, a segment method, etc. are mentioned, for example. Also, the matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are two-dimensionally arranged in a lattice or mosaic form, and characters or images are displayed by a set of pixels. The shape or size of the pixel is determined according to the purpose. For example, for displaying images and characters on computers, monitors, and televisions, square pixels with a side of 300 μm or less are usually used, and in the case of a large display such as a display panel, pixels on the order of mm are used. do. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, red, green, and blue pixels are arranged and displayed. In this case, there are typically a delta type and a stripe type. Incidentally, as a driving method for this matrix, either a line-sequential driving method or an active matrix may be used. Line-sequential driving has the advantage of having a simple structure, but when operating characteristics are taken into consideration, the active matrix may be superior, so it is necessary to use this also according to the purpose.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is illuminated. For example, the time or temperature display in a digital watch or thermometer, the operation state display of an audio device or electric cooker, and the panel display of a car etc. are mentioned.

Examples of the lighting device include lighting devices such as indoor lighting, backlights of liquid crystal display devices, and the like (for example, Japanese Patent Laid-Open No. 2003-257621, Japanese Patent Laid-Open No. 2003-277741, Japanese Patent). Publication No. 2004-119211, etc.). Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light themselves, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display panels, and signs. In particular, considering that it is difficult to reduce the thickness of a liquid crystal display device, especially a backlight for a computer where thinning is a problem, because the conventional method consists of a fluorescent lamp or a light guide plate, the backlight using the light emitting element according to the present embodiment is thin. and is characterized by being lightweight.

3-2. other organic devices

The polycyclic aromatic compound according to the present invention can be used for fabrication of an organic field effect transistor or an organic thin film solar cell in addition to the organic electroluminescent device described above.

[Example]

Hereinafter, the present invention will be described more specifically by way of examples, but the present invention is not limited thereto. First, synthesis examples of polycyclic aromatic compounds are described below.

Synthesis Example 1: Synthesis of the compound represented by compound (1a-43)

Compound (X-1) (2.0 g), Compound (X-2) (1.56 g), dichlorobistriphenylphosphine palladium (0.09 g), tetrabutylammonium bromide (TBAB) (0.42 g), potassium carbonate (1.81 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (0.74 g) represented by the formula (1a-43Y) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

¹ H-NMR (500 Mz, CDCl ₃ )δ=9.2229 (d, 2H), 8.082 (d, 2H), 8.053-8.030 (m, 4H), 7.696-7.624 (m, 3H), 7.521 (t, 2H) , 7.445-7.375 (m, 4H), 7.273-7.172 (m, 6H), 7.091 (t, 1H), 6.849 (t, 2H), 6.584 (d, 2H).

MALDI-TOF-MS(M+H)=653.76

Synthesis Example 2: Synthesis of compound represented by formula (1a-14)

Compound (X-3) (3.0 g), Compound (X-2) (2.34 g), dichlorobistriphenylphosphine palladium (0.14 g), tetrabutylammonium bromide (TBAB) (0.63 g), potassium carbonate (2.71 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (2.71 g) represented by the formula (1a-14) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

¹ H-NMR (500 Mz, CDCl ₃ )δ=8.764 (d, 2H), 8.627 (d, 1H), 8.557 (d, 2H), 7.997 (d, 2H), 7.908 (d, 2H), 7.839 (d , 1H), 7.593(t, 1H), 7.542(t, 2H), 7.459-7.415(m, 5H), 7.375(t, 2H), 7.309-7.219(m, 6H), 6.839(t, 1H), 6.478(d, 1H).

MALDI-TOF-MS(M+H)=653.76

Synthesis Example 3: Synthesis of compound represented by formula (2q-1)

Compound (X-4) (3.0 g), Compound (X-2) (2.34 g), dichlorobistriphenylphosphine palladium (0.14 g), tetrabutylammonium bromide (TBAB) (0.63 g), potassium carbonate (2.71 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (2.71 g) represented by the formula (2q-1) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

MALDI-TOF-MS(M+H)=653.76

Synthesis Example 4: Synthesis of compound represented by formula (1a-22)

Compound (X-3) (2.0 g), Compound (X-5) (1.95 g), dichlorobistriphenylphosphine palladium (0.09 g), tetrabutylammonium bromide (TBAB) (0.42 g), potassium carbonate (1.81 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (1.02 g) represented by the formula (1a-22) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

¹ H-NMR (500 Mz, CDCl ₃ )δ=8.731 (d, 4H), 8.587 (d, 1H), 8.024 (d, 4H), 7.898 (d, 2H), 7.863 (d, 1H), 7.494 (d , 1H), 7.453-7.359 (m, 10H), 7.317-7.224 (m, 6H), 6.839 (t, 1H), 6.451 (d, 1H).

MALDI-TOF-MS(M+H)=742.85

Synthesis Example 5: Synthesis of compound represented by formula (1h-15)

Compound (X-6) (5.0 g), Compound (X-2) (3.88 g), dichlorobistriphenylphosphine palladium (0.25 g), tetrabutylammonium bromide (TBAB) (1.05 g), potassium carbonate (4.50 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (3.88 g) represented by the formula (1h-15) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

¹ H-NMR (500 Mz, CDCl ₃ )δ=8.931 (d, 2H), 8.680 (d, 1H), 8.589 (d, 2H), 8.457 (d, 1H), 8.018 (d, 2H), 7.610 (t , 1H), 7.558 (t, 2H), 7.391-7.243 (m, 11H), 7.144-7.103 (m, 5H), 7.003 (d, 1H).

MALDI-TOF-MS(M+H)=655.77

Synthesis Example 6: Synthesis of compound represented by formula (1j-31)

Compound (X-7) (3.0 g), Compound (X-2) (2.00 g), dichlorobistriphenylphosphine palladium (0.12 g), tetrabutylammonium bromide (TBAB) (0.54 g), potassium carbonate (2.32 g) g), toluene (30.0 ml) and water (30.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (2.25 g) represented by the formula (1j-31) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

MALDI-TOF-MS(M+H)=729.89

Synthesis Example 7: Synthesis of compound represented by formula (1a-20)

Compound (X-8) (5.0 g), Compound (X-2) (2.86 g), dichlorobistriphenylphosphine palladium (0.17 g), tetrabutylammonium bromide (TBAB) (0.77 g), potassium carbonate (3.32 g) g), toluene (50.0 ml) and water (50.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (2.29 g) represented by the formula (1a-20) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

MALDI-TOF-MS(M+H)=819.04

Synthesis Example 8: Synthesis of compound represented by formula (1a-28)

Compound (X-9) (2.0 g), Compound (X-2) (1.39 g), dichlorobistriphenylphosphine palladium (0.07 g), tetrabutylammonium bromide (TBAB) (0.30 g), potassium carbonate (1.29 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (1.07 g) represented by the formula (1a-28) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

MALDI-TOF-MS(M+H)=925.09

Synthesis Example 9: Synthesis of compound represented by formula (1a-23)

Compound (X-10) (3.0 g), Compound (X-5) (2.14 g), dichlorobistriphenylphosphine palladium (0.10 g), tetrabutylammonium bromide (TBAB) (0.46 g), potassium carbonate (1.99 g) g), toluene (30.0 ml) and water (30.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (1.53 g) represented by the formula (1a-23) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

MALDI-TOF-MS(M+H)=908.03

Synthesis Example 10: Synthesis of Compound Represented by Formula (1b-8)

Compound (X-11) (2.0 g), Compound (X-5) (2.69 g), dichlorobistriphenylphosphine palladium (0.13 g), tetrabutylammonium bromide (TBAB) (0.58 g), potassium carbonate (2.50 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (1.70 g) represented by formula (1b-8) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

MALDI-TOF-MS(M+H)=741.87

Synthesis Example 11: Synthesis of Compound Represented by Formula (1d-20)

Compound (X-12) (2.0 g), Compound (X-5) (1.88 g), dichlorobistriphenylphosphine palladium (0.09 g), tetrabutylammonium bromide (TBAB) (0.41 g), potassium carbonate (1.75 g) g), toluene (20.0 ml) and water (20.0 ml) were added, and the mixture was heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). A compound (0.96 g) represented by the formula (1d-20) was obtained by distilling off the solvent in a fraction containing the target object under reduced pressure.

MALDI-TOF-MS(M+H)=758.92

Other polycyclic aromatic compounds of the present invention can be synthesized by a method according to the synthesis example described above by appropriately changing the compound of the raw material.

Next, fabrication and evaluation of an organic EL device using the compound of the present invention will be described. However, the application of the compound of the present invention is not limited to the examples shown below, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical properties of the compound of the present invention.

<Comparative Example 1-1>

A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) obtained by polishing ITO film formed to a thickness of 200 nm by sputtering to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and HAT-CN, HTL-1, TcTa, mCBP, ETL-1, and ET7 were placed respectively for molybdenum deposition. A boat for evaporation made of tungsten, each containing LiF and aluminum, was installed.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5×10 ^-4 Pa, and first, HAT-CN was heated and deposited to a thickness of 5 nm to form a hole injection layer. Next, HTL-1 was heated and deposited to a film thickness of 90 nm to form a hole transport layer 1, and further, TcTa was heated and deposited to a film thickness of 10 nm to form a hole transport layer 2. Next, mCBP and new-DABNA were simultaneously heated and deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the mass ratio of mCBP and new-DABNA was about 99:1. Next, ETL-1 was heated and deposited to a film thickness of 20 nm to form an electron transport layer 1, and further, ET7 was heated and deposited to a film thickness of 10 nm to form an electron transport layer 2. The deposition rate of each layer was 0.01 to 1 nm/sec. After that, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then aluminum was heated and deposited to a film thickness of 100 nm to form a cathode to obtain an organic EL device. At this time, the deposition rate of aluminum was adjusted to be 1 to 10 nm/sec.

<Example 1-1 to Example 1-11, Example 2-1 to Example 2-2, Comparative Example 1-2 to Comparative Example 1-3>

Host 1 or electron transport layer 1 of Comparative Example 1-1 was changed to each material shown in Table 1, and each element was fabricated.

The chemical structure of the compound used is shown below.

External quantum efficiency of the fabricated organic EL device at a luminance of 1000 cd/m ² , and LT50 (time until 500 cd/m ² is reached when continuously driven at a current density at an initial luminance of 1000 cd/m ² ) was measured. Table 2 shows the evaluation results of each element.

From the comparison with Comparative Examples, it is found that high efficiency and long lifetime can be obtained when a polycyclic aromatic compound having a structure containing the structural unit represented by Formula (1) is used for the host or the electron transport layer.

<Example 3-1 to Example 3-4, Example 4-1 to Example 4-4 and Comparative Example 3-1>

Host 1 of Comparative Example 1-1 was changed to Host 1 and Host 2 at the concentrations shown in Table 3, and electron transport layer 1 was made of each material shown in Table 3, and each element was fabricated. On the other hand, in each table below, "Host 1" corresponds to an electron-transporting host material, and "Host 2" corresponds to a hole-transporting host material.

External quantum efficiency of the fabricated organic EL device at a luminance of 1000 cd/m ² , and LT50 (time until 500 cd/m ² is reached when continuously driven at a current density at an initial luminance of 1000 cd/m ² ) was measured. Table 4 shows the evaluation results of each element.

From the comparison with Comparative Examples, it can be seen that high efficiency and long lifetime can be obtained when a polycyclic aromatic compound having a structure containing the structural unit represented by Formula (1) is used as one component of the host or electron transport layer.

<Comparative Example 5-1>

A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) obtained by polishing ITO film formed to a thickness of 200 nm by sputtering to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and HAT-CN, HTL-1, T2T, TcTa, BCC-TPTA, ETL-1, and ET7 were respectively inserted. A boat for evaporation made of molybdenum and a boat for evaporation made of tungsten containing LiF and aluminum were installed.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5×10 ^-4 Pa, and first, HAT-CN was heated and deposited to a film thickness of 5 nm to form a hole injection layer. Next, HTL-1 was heated and deposited to a film thickness of 90 nm to form a hole transport layer 1, and further, TcTa was heated and deposited to a film thickness of 10 nm to form a hole transport layer 2. Next, T2T, TcTa, BCC-TPTA, and new-DABNA were simultaneously heated and deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the mass ratio of T2T, TcTa, BCC-TPTA, and new-DABNA was about 44.5:44.5:10:1. Next, ETL-1 was heated and deposited to a film thickness of 20 nm to form an electron transport layer 1, and further, ET7 was heated and deposited to a film thickness of 10 nm to form an electron transport layer 2. The deposition rate of each layer was 0.01 to 1 nm/sec. After that, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then aluminum was heated and deposited to a film thickness of 100 nm to form a cathode to obtain an organic EL device. At this time, the deposition rate of aluminum was adjusted to be 1 to 10 nm/sec.

<Example 5-1 to Example 5-3, and Example 6-1 to Example 6-3>

Each element was fabricated by changing the composition of the light emitting layer of Comparative Example 5-1 to the materials and concentrations shown in Table 5.

External quantum efficiency of the fabricated organic EL device at a luminance of 1000 cd/m ² , and LT50 (time until 500 cd/m ² is reached when continuously driven at a current density at an initial luminance of 1000 cd/m ² ) was measured. Table 6 shows the evaluation results of each element.

From the comparison with Comparative Examples, it is found that high efficiency and long lifetime can be obtained when a polycyclic aromatic compound having a structure containing the structural unit represented by Formula (1) is used as one component of the host.

100 organic electroluminescent device
101 substrate
102 anode
103 hole injection layer
104 hole transport layer
105 light emitting layer
106 electron transport layer
107 electron injection layer
108 Cathode

Claims (11)

polycyclic aromatic compounds having a structure composed of one or two or more structural units represented by the following formula (1);

In formula (1),
A is a monovalent group obtained by elimination of one hydrogen in the compound represented by formula (A),
Z is each independently >N or >CR ^Z ;
R ^Z are each independently hydrogen or any one substituent selected from substituent group Z,
Two adjacent R ^Z are bonded to each other, together with the carbon to which they are bonded, an aryl ring which may be substituted with at least one substituent selected from substituent group Z, or an aryl ring which may be substituted with at least one substituent selected from substituent group Z. may form a heteroaryl ring that is
Z ^X is carbon bonded by the other Z ^X and X ² , or >N or >CR ^Z ;
X ¹ and X ² are each independently a single bond, >O, >NR ^N1 , >BR ^B1 , >C(-R ^C1 ) ₂ , >Si(-R ^S1 ) ₂ , >S, >Se, -CR ^E1 =CR ^E1 -, or 1,2-phenylene, provided that when X ¹ is a single bond, X ² is not a single bond;
R ^N1 , R ^B1 and R ^E1 are each independently hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, Alkyl which may be substituted with at least one substituent selected from substituent group Z, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, R ^C1 and R ^S1 are each independently hydrogen, substituent group Aryl which may be substituted with at least one substituent selected from Z, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, or bonded to another R ^C1 or R ^S1 bonded to the same element to form a ring;
W is C, Si, or Ge;
Ring B is an aryl ring which may be substituted with at least one substituent selected from substituent group Z, or a heteroaryl ring which may be substituted with at least one substituent selected from substituent group Z,
at least one Y is >N,
at least one Y is >CG, G is a group represented by formula (G);

In formula (G),
Z ^Y is >N or >CR ^Z ,
X ⁶ is a single bond, >C(-R ^C6 ) ₂ , >S, >O, >NR ^N6 , >Si(-R ^S6 ) ₂ , >Se, >Ge(-R ^G6 ) ₂ , -CR ^E6 =CR ^E6 -, or 1,2-phenylene, * is a binding site,
R ^N6 is hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, and at least one selected from substituent group Z Alkyl which may be substituted with a substituent, or cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, R ^C6 , R ^S6 , and R ^G6 are each independently hydrogen, at least one selected from substituent group Z Aryl which may be substituted with one substituent, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or substituent group Z Cycloalkyl which may be substituted with at least one selected substituent, or is bonded to another R ^C6 , R ^S6 , or R ^G6 bonded to the same element to form a ring, and R ^E6 is hydrogen, in substituent group Z aryl which may be substituted with at least one substituent selected from, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or substituent A cycloalkyl which may be substituted with at least one substituent selected from group Z,
the other Y's are each independently >CR ^Y ,
R ^Y is each independently hydrogen or a substituent selected from substituent group Z, R ^Y is a group other than the group represented by formula (G),
L is a single bond, arylene, heteroarylene, >O, >NR ^NL , >BR ^BL , >C(-R ^CL ) ₂ , >Si(-R ^SL ) ₂ , >S, or >Se;
R ^NL and R ^BL are hydrogen, aryl optionally substituted with at least one substituent selected from substituent group Z, heteroaryl optionally substituted with at least one substituent selected from substituent group Z, and at least one selected from substituent group Z Alkyl which may be substituted with one substituent, cycloalkyl which may be substituted with at least one substituent selected from substituent group Z, R ^CL and R ^SL are each independently hydrogen, at least one substituent selected from substituent group Z aryl which may be substituted with, heteroaryl which may be substituted with at least one substituent selected from substituent group Z, alkyl which may be substituted with at least one substituent selected from substituent group Z, or at least one selected from substituent group Z Cycloalkyl which may be substituted with one substituent, or bonded to another R ^CL or R ^SL bonded to the same element to form a ring;
At least one hydrogen in the above structure may be substituted with cyano, halogen, or deuterium,
Substituent group Z is,
aryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
heteroaryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
diarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded to each other via a linking group);
diheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two heteroaryls may be bonded to each other via a linking group);
Arylheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (aryl and heteroaryl may be bonded to each other via a linking group);
diarylboryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded via a single bond or a linking group);
Alkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
cycloalkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
alkoxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
aryloxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl, and
It consists of substituted silyl. According to claim 1,
A polycyclic aromatic compound in which X ⁶ is a single bond. According to claim 1 or 2,
polycyclic aromatic compounds having the following partial structures;

In the formula, R ^G is R ^Y or G, and is bonded to L at *. According to claim 3,
A polycyclic aromatic compound in which R ^G is phenyl or a group represented by formula (G). According to claim 1,
A polycyclic aromatic compound represented by any one of the following formulas.

A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 5. An organic electroluminescent device comprising a pair of electrodes comprising an anode and a cathode, and an organic layer disposed between the pair of electrodes, wherein the organic layer contains the polycyclic aromatic compound according to any one of claims 1 to 5. . According to claim 7,
An organic electroluminescent device in which the organic layer is a light emitting layer. According to claim 8,
The organic electroluminescent device, wherein the light emitting layer includes the polycyclic aromatic compound as a host material and further includes a dopant material. According to claim 7,
The organic electroluminescent device, wherein the organic layer is an electron transport layer. A display device or lighting device provided with the organic electroluminescent device according to any one of claims 7 to 10.

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